organic compounds
1-Benzyl-3-methylquinoxalin-2(1H)-one
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
The 16H14N2O, 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.
of the title compound, CKeywords: crystal structure; quinoxaline; hydrogen bonds; π-stacking.
CCDC reference: 1827953
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). 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; Wang et al., 2007; Bérubé et al., 2015; Ramli & Essassi, 2015). 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, 2013, 2017; Caleb et al., 2016), the title compound (Fig. 1) was synthesized and its structure is reported here.
The ) 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)°.
of the title compound (Fig. 1In the crystal, each independent molecule forms a stack, with each stack oriented approximately along the a-axis direction (Fig. 2). 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. 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 (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 and Fig. 2 (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 (center)]. These dimers are connected only by pairwise C44—H44⋯N5 hydrogen bonds (Table 1) 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 and Fig. 3).
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 .
details are summarized in Table 2
|
Structural data
CCDC reference: 1827953
https://doi.org/10.1107/S2414314618003905/sj4167sup1.cif
contains datablocks global, I. DOI: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
Data collection: APEX3 (Bruker, 2016); cell
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).C16H14N2O | Z = 6 |
Mr = 250.29 | F(000) = 792 |
Triclinic, P1 | Dx = 1.269 Mg m−3 |
a = 7.3502 (4) Å | Mo Kα radiation, λ = 0.71073 Å |
b = 17.3508 (10) Å | Cell parameters from 9979 reflections |
c = 17.9449 (10) Å | θ = 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) Å3 | 0.33 × 0.27 × 0.24 mm |
Bruker SMART APEX CCD diffractometer | 9752 independent reflections |
Radiation source: fine-focus sealed tube | 7343 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.032 |
Detector resolution: 8.3333 pixels mm-1 | θmax = 28.4°, θmin = 2.3° |
φ and ω scans | h = −9→9 |
Absorption correction: multi-scan (SADABS; Bruker, 2016) | k = −23→23 |
Tmin = 0.88, Tmax = 0.98 | l = −23→23 |
36858 measured reflections |
Refinement on F2 | Primary atom site location: structure-invariant direct methods |
Least-squares matrix: full | Secondary atom site location: difference Fourier map |
R[F2 > 2σ(F2)] = 0.045 | Hydrogen site location: difference Fourier map |
wR(F2) = 0.124 | All 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 parameters | Δρmax = 0.40 e Å−3 |
0 restraints | Δρmin = −0.19 e Å−3 |
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. |
x | y | z | Uiso*/Ueq | ||
O1 | 0.25912 (12) | 0.20951 (5) | 0.59094 (5) | 0.0277 (2) | |
N1 | 0.21470 (13) | −0.00884 (6) | 0.56016 (6) | 0.0194 (2) | |
N2 | 0.29459 (13) | 0.08246 (6) | 0.47301 (6) | 0.0195 (2) | |
C1 | 0.28682 (15) | −0.00957 (7) | 0.43184 (7) | 0.0179 (2) | |
C2 | 0.31828 (16) | −0.05831 (8) | 0.34823 (7) | 0.0215 (2) | |
H2 | 0.3438 (19) | −0.0299 (8) | 0.3147 (9) | 0.029 (4)* | |
C3 | 0.31140 (16) | −0.14907 (8) | 0.31127 (7) | 0.0237 (2) | |
H3 | 0.3302 (18) | −0.1825 (8) | 0.2505 (8) | 0.026 (3)* | |
C4 | 0.27393 (16) | −0.19281 (7) | 0.35604 (7) | 0.0233 (2) | |
H4 | 0.2685 (18) | −0.2559 (9) | 0.3295 (8) | 0.025 (3)* | |
C5 | 0.23991 (16) | −0.14547 (7) | 0.43800 (7) | 0.0208 (2) | |
H5 | 0.2113 (19) | −0.1747 (9) | 0.4715 (9) | 0.029 (3)* | |
C6 | 0.24551 (15) | −0.05360 (7) | 0.47658 (7) | 0.0184 (2) | |
C7 | 0.22057 (15) | 0.07611 (7) | 0.59656 (7) | 0.0189 (2) | |
C8 | 0.25818 (15) | 0.12892 (7) | 0.55450 (7) | 0.0202 (2) | |
C9 | 0.19308 (18) | 0.12631 (8) | 0.68734 (8) | 0.0245 (3) | |
H9A | 0.306 (3) | 0.1689 (10) | 0.7257 (11) | 0.053 (5)* | |
H9B | 0.168 (2) | 0.0877 (10) | 0.7109 (10) | 0.038 (4)* | |
H9C | 0.089 (2) | 0.1611 (10) | 0.6900 (10) | 0.050 (5)* | |
C10 | 0.35018 (17) | 0.13201 (8) | 0.43105 (8) | 0.0236 (2) | |
H10A | 0.4637 (19) | 0.1114 (8) | 0.4100 (8) | 0.026 (3)* | |
H10B | 0.3824 (19) | 0.1958 (9) | 0.4787 (9) | 0.027 (3)* | |
C11 | 0.20033 (17) | 0.12470 (7) | 0.35751 (7) | 0.0217 (2) | |
C12 | 0.25335 (19) | 0.14397 (8) | 0.29634 (8) | 0.0269 (3) | |
H12 | 0.388 (2) | 0.1614 (9) | 0.3015 (9) | 0.031 (4)* | |
C13 | 0.1197 (2) | 0.14019 (8) | 0.22947 (8) | 0.0309 (3) | |
H13 | 0.157 (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)* | |
C16 | 0.01263 (17) | 0.10252 (8) | 0.35061 (8) | 0.0250 (3) | |
H16 | −0.0264 (19) | 0.0896 (9) | 0.3916 (9) | 0.031 (4)* | |
O2 | 0.83756 (12) | 0.44828 (6) | 0.14776 (5) | 0.0288 (2) | |
N3 | 0.82391 (13) | 0.56950 (6) | 0.03367 (6) | 0.0203 (2) | |
N4 | 0.68101 (13) | 0.40490 (6) | 0.00926 (6) | 0.0183 (2) | |
C17 | 0.64388 (15) | 0.42244 (7) | −0.05980 (7) | 0.0166 (2) | |
C18 | 0.53684 (15) | 0.36034 (7) | −0.14181 (7) | 0.0203 (2) | |
H18 | 0.4877 (19) | 0.3022 (9) | −0.1507 (8) | 0.029 (4)* | |
C19 | 0.50247 (16) | 0.38126 (8) | −0.20784 (7) | 0.0226 (2) | |
H19 | 0.4289 (19) | 0.3372 (9) | −0.2623 (9) | 0.027 (3)* | |
C20 | 0.57138 (16) | 0.46423 (8) | −0.19377 (7) | 0.0233 (2) | |
H20 | 0.5407 (19) | 0.4772 (8) | −0.2406 (9) | 0.029 (4)* | |
C21 | 0.67822 (17) | 0.52534 (8) | −0.11371 (7) | 0.0219 (2) | |
H21 | 0.7310 (19) | 0.5837 (9) | −0.1041 (8) | 0.026 (3)* | |
C22 | 0.71649 (15) | 0.50512 (7) | −0.04612 (7) | 0.0176 (2) | |
C23 | 0.86029 (15) | 0.55100 (7) | 0.09630 (7) | 0.0200 (2) | |
C24 | 0.79521 (15) | 0.46502 (7) | 0.08829 (7) | 0.0197 (2) | |
C25 | 0.97279 (18) | 0.61937 (8) | 0.18262 (8) | 0.0258 (3) | |
H25A | 0.900 (2) | 0.6396 (9) | 0.2251 (9) | 0.036 (4)* | |
H25B | 1.013 (2) | 0.6728 (10) | 0.1804 (10) | 0.045 (4)* | |
H25C | 1.077 (2) | 0.5944 (10) | 0.2035 (10) | 0.044 (4)* | |
C26 | 0.59944 (17) | 0.32168 (7) | −0.00011 (8) | 0.0223 (2) | |
H26A | 0.605 (2) | 0.3317 (9) | 0.0589 (10) | 0.033 (4)* | |
H26B | 0.4654 (19) | 0.3103 (8) | −0.0276 (8) | 0.023 (3)* | |
C27 | 0.69508 (17) | 0.24355 (7) | −0.05122 (7) | 0.0215 (2) | |
C28 | 0.87161 (17) | 0.25453 (8) | −0.06534 (7) | 0.0231 (2) | |
H28 | 0.9364 (19) | 0.3148 (9) | −0.0435 (8) | 0.026 (3)* | |
C29 | 0.95776 (19) | 0.18102 (8) | −0.10981 (7) | 0.0273 (3) | |
H29 | 1.083 (2) | 0.1914 (9) | −0.1200 (9) | 0.033 (4)* | |
C30 | 0.8698 (2) | 0.09670 (8) | −0.13975 (8) | 0.0329 (3) | |
H30 | 0.932 (2) | 0.0436 (9) | −0.1720 (9) | 0.038 (4)* | |
C31 | 0.6934 (2) | 0.08534 (9) | −0.12627 (9) | 0.0385 (3) | |
H31 | 0.634 (2) | 0.0259 (11) | −0.1465 (10) | 0.051 (5)* | |
C32 | 0.6049 (2) | 0.15839 (8) | −0.08264 (9) | 0.0327 (3) | |
H32 | 0.478 (2) | 0.1501 (10) | −0.0735 (10) | 0.045 (4)* | |
O3 | 0.64780 (13) | 0.26946 (5) | 0.40946 (6) | 0.0306 (2) | |
N5 | 0.76117 (13) | 0.49974 (6) | 0.55516 (6) | 0.0207 (2) | |
N6 | 0.71477 (13) | 0.37944 (6) | 0.37836 (6) | 0.0201 (2) | |
C33 | 0.75948 (15) | 0.46950 (7) | 0.40722 (7) | 0.0191 (2) | |
C34 | 0.78126 (16) | 0.50245 (8) | 0.35079 (8) | 0.0242 (2) | |
H34 | 0.7675 (19) | 0.4622 (9) | 0.2889 (9) | 0.029 (3)* | |
C35 | 0.82796 (17) | 0.59192 (9) | 0.38409 (9) | 0.0279 (3) | |
H35 | 0.8423 (19) | 0.6146 (9) | 0.3469 (9) | 0.029 (3)* | |
C36 | 0.85515 (17) | 0.65104 (8) | 0.47278 (9) | 0.0281 (3) | |
H36 | 0.891 (2) | 0.7136 (9) | 0.4944 (9) | 0.033 (4)* | |
C37 | 0.83184 (17) | 0.61908 (8) | 0.52814 (8) | 0.0234 (2) | |
H37 | 0.8481 (19) | 0.6572 (9) | 0.5903 (9) | 0.029 (3)* | |
C38 | 0.78320 (15) | 0.52840 (7) | 0.49630 (7) | 0.0195 (2) | |
C39 | 0.71728 (16) | 0.41640 (7) | 0.52664 (7) | 0.0211 (2) | |
C40 | 0.68970 (16) | 0.34819 (7) | 0.43423 (7) | 0.0215 (2) | |
C41 | 0.6911 (2) | 0.38403 (9) | 0.58826 (9) | 0.0291 (3) | |
H41A | 0.762 (2) | 0.3343 (10) | 0.5804 (10) | 0.041 (4)* | |
H41B | 0.559 (2) | 0.3606 (10) | 0.5773 (10) | 0.048 (4)* | |
H41C | 0.732 (2) | 0.4319 (10) | 0.6481 (11) | 0.045 (4)* | |
C42 | 0.69186 (17) | 0.31401 (8) | 0.28656 (7) | 0.0252 (3) | |
H42A | 0.7162 (18) | 0.2580 (9) | 0.2844 (8) | 0.027 (3)* | |
H42B | 0.788 (2) | 0.3291 (8) | 0.2620 (9) | 0.029 (4)* | |
C43 | 0.50068 (16) | 0.30338 (7) | 0.23189 (7) | 0.0211 (2) | |
C44 | 0.36495 (17) | 0.35469 (8) | 0.26581 (8) | 0.0236 (2) | |
H44 | 0.3899 (18) | 0.3989 (9) | 0.3280 (9) | 0.026 (3)* | |
C45 | 0.19109 (18) | 0.34284 (8) | 0.21381 (9) | 0.0279 (3) | |
H45 | 0.095 (2) | 0.3820 (9) | 0.2385 (9) | 0.037 (4)* | |
C46 | 0.14965 (19) | 0.27846 (9) | 0.12749 (8) | 0.0309 (3) | |
H46 | 0.030 (2) | 0.2697 (9) | 0.0929 (9) | 0.036 (4)* | |
C47 | 0.2840 (2) | 0.22663 (9) | 0.09300 (8) | 0.0328 (3) | |
H47 | 0.257 (2) | 0.1820 (10) | 0.0335 (11) | 0.044 (4)* | |
C48 | 0.45847 (18) | 0.23918 (8) | 0.14456 (8) | 0.0269 (3) | |
H48 | 0.551 (2) | 0.2010 (9) | 0.1180 (9) | 0.030 (4)* |
U11 | U22 | U33 | U12 | U13 | U23 | |
O1 | 0.0357 (5) | 0.0181 (4) | 0.0258 (4) | 0.0043 (3) | 0.0032 (4) | 0.0090 (3) |
N1 | 0.0185 (5) | 0.0203 (4) | 0.0177 (4) | 0.0015 (4) | 0.0023 (4) | 0.0086 (4) |
N2 | 0.0207 (5) | 0.0179 (4) | 0.0193 (5) | 0.0004 (4) | 0.0020 (4) | 0.0095 (4) |
C1 | 0.0136 (5) | 0.0195 (5) | 0.0188 (5) | 0.0011 (4) | 0.0005 (4) | 0.0089 (4) |
C2 | 0.0182 (6) | 0.0264 (6) | 0.0198 (5) | 0.0021 (4) | 0.0026 (4) | 0.0118 (5) |
C3 | 0.0178 (6) | 0.0274 (6) | 0.0178 (5) | 0.0050 (5) | 0.0017 (4) | 0.0052 (5) |
C4 | 0.0205 (6) | 0.0183 (5) | 0.0232 (6) | 0.0036 (4) | −0.0008 (5) | 0.0056 (5) |
C5 | 0.0173 (6) | 0.0200 (5) | 0.0228 (6) | 0.0005 (4) | −0.0010 (4) | 0.0105 (5) |
C6 | 0.0143 (5) | 0.0204 (5) | 0.0181 (5) | 0.0015 (4) | 0.0002 (4) | 0.0086 (4) |
C7 | 0.0137 (5) | 0.0223 (5) | 0.0180 (5) | 0.0013 (4) | −0.0003 (4) | 0.0092 (4) |
C8 | 0.0181 (6) | 0.0195 (5) | 0.0196 (5) | 0.0022 (4) | −0.0009 (4) | 0.0085 (4) |
C9 | 0.0254 (7) | 0.0255 (6) | 0.0194 (6) | 0.0038 (5) | 0.0036 (5) | 0.0088 (5) |
C10 | 0.0243 (6) | 0.0242 (6) | 0.0245 (6) | −0.0013 (5) | 0.0032 (5) | 0.0147 (5) |
C11 | 0.0277 (6) | 0.0157 (5) | 0.0209 (5) | 0.0034 (4) | 0.0051 (5) | 0.0084 (4) |
C12 | 0.0335 (7) | 0.0221 (6) | 0.0275 (6) | 0.0002 (5) | 0.0078 (5) | 0.0138 (5) |
C13 | 0.0472 (9) | 0.0239 (6) | 0.0268 (6) | 0.0059 (5) | 0.0083 (6) | 0.0163 (5) |
C14 | 0.0415 (8) | 0.0260 (6) | 0.0249 (6) | 0.0135 (5) | 0.0029 (6) | 0.0128 (5) |
C15 | 0.0276 (7) | 0.0318 (6) | 0.0299 (7) | 0.0099 (5) | 0.0062 (5) | 0.0145 (5) |
C16 | 0.0276 (7) | 0.0263 (6) | 0.0247 (6) | 0.0063 (5) | 0.0079 (5) | 0.0144 (5) |
O2 | 0.0324 (5) | 0.0361 (5) | 0.0211 (4) | 0.0093 (4) | 0.0047 (4) | 0.0165 (4) |
N3 | 0.0183 (5) | 0.0192 (4) | 0.0191 (5) | 0.0026 (4) | 0.0053 (4) | 0.0056 (4) |
N4 | 0.0203 (5) | 0.0179 (4) | 0.0161 (4) | 0.0033 (4) | 0.0042 (4) | 0.0077 (4) |
C17 | 0.0152 (5) | 0.0195 (5) | 0.0158 (5) | 0.0057 (4) | 0.0057 (4) | 0.0081 (4) |
C18 | 0.0180 (6) | 0.0204 (5) | 0.0190 (5) | 0.0032 (4) | 0.0044 (4) | 0.0065 (4) |
C19 | 0.0177 (6) | 0.0282 (6) | 0.0168 (5) | 0.0067 (5) | 0.0031 (4) | 0.0070 (5) |
C20 | 0.0228 (6) | 0.0328 (6) | 0.0197 (5) | 0.0122 (5) | 0.0082 (5) | 0.0153 (5) |
C21 | 0.0236 (6) | 0.0233 (5) | 0.0237 (6) | 0.0079 (5) | 0.0102 (5) | 0.0134 (5) |
C22 | 0.0157 (5) | 0.0185 (5) | 0.0167 (5) | 0.0040 (4) | 0.0057 (4) | 0.0062 (4) |
C23 | 0.0167 (5) | 0.0225 (5) | 0.0174 (5) | 0.0050 (4) | 0.0058 (4) | 0.0062 (4) |
C24 | 0.0171 (5) | 0.0245 (5) | 0.0164 (5) | 0.0070 (4) | 0.0051 (4) | 0.0084 (4) |
C25 | 0.0223 (6) | 0.0268 (6) | 0.0185 (6) | 0.0013 (5) | 0.0028 (5) | 0.0041 (5) |
C26 | 0.0264 (7) | 0.0195 (5) | 0.0226 (6) | 0.0040 (5) | 0.0094 (5) | 0.0103 (5) |
C27 | 0.0299 (6) | 0.0192 (5) | 0.0164 (5) | 0.0055 (4) | 0.0054 (5) | 0.0093 (4) |
C28 | 0.0272 (6) | 0.0240 (6) | 0.0166 (5) | 0.0055 (5) | 0.0015 (5) | 0.0096 (5) |
C29 | 0.0299 (7) | 0.0319 (6) | 0.0176 (5) | 0.0109 (5) | 0.0031 (5) | 0.0104 (5) |
C30 | 0.0489 (9) | 0.0250 (6) | 0.0248 (6) | 0.0157 (6) | 0.0091 (6) | 0.0111 (5) |
C31 | 0.0591 (10) | 0.0203 (6) | 0.0363 (8) | 0.0065 (6) | 0.0166 (7) | 0.0121 (6) |
C32 | 0.0421 (8) | 0.0249 (6) | 0.0330 (7) | 0.0035 (6) | 0.0138 (6) | 0.0139 (5) |
O3 | 0.0319 (5) | 0.0207 (4) | 0.0352 (5) | −0.0005 (4) | 0.0054 (4) | 0.0114 (4) |
N5 | 0.0208 (5) | 0.0230 (5) | 0.0196 (5) | 0.0052 (4) | 0.0055 (4) | 0.0108 (4) |
N6 | 0.0197 (5) | 0.0198 (4) | 0.0176 (5) | 0.0036 (4) | 0.0036 (4) | 0.0067 (4) |
C33 | 0.0153 (5) | 0.0213 (5) | 0.0206 (5) | 0.0043 (4) | 0.0026 (4) | 0.0105 (4) |
C34 | 0.0185 (6) | 0.0355 (6) | 0.0218 (6) | 0.0048 (5) | 0.0022 (5) | 0.0171 (5) |
C35 | 0.0216 (6) | 0.0387 (7) | 0.0359 (7) | 0.0055 (5) | 0.0035 (5) | 0.0289 (6) |
C36 | 0.0236 (6) | 0.0241 (6) | 0.0399 (7) | 0.0044 (5) | 0.0025 (5) | 0.0197 (6) |
C37 | 0.0217 (6) | 0.0217 (5) | 0.0250 (6) | 0.0053 (4) | 0.0034 (5) | 0.0103 (5) |
C38 | 0.0165 (5) | 0.0221 (5) | 0.0210 (5) | 0.0051 (4) | 0.0043 (4) | 0.0112 (5) |
C39 | 0.0179 (6) | 0.0247 (5) | 0.0228 (6) | 0.0045 (4) | 0.0057 (4) | 0.0128 (5) |
C40 | 0.0183 (6) | 0.0219 (5) | 0.0240 (6) | 0.0031 (4) | 0.0034 (4) | 0.0112 (5) |
C41 | 0.0318 (7) | 0.0330 (7) | 0.0300 (7) | 0.0032 (6) | 0.0115 (6) | 0.0198 (6) |
C42 | 0.0236 (6) | 0.0261 (6) | 0.0191 (6) | 0.0071 (5) | 0.0054 (5) | 0.0051 (5) |
C43 | 0.0235 (6) | 0.0213 (5) | 0.0189 (5) | 0.0009 (4) | 0.0040 (4) | 0.0105 (4) |
C44 | 0.0241 (6) | 0.0228 (5) | 0.0232 (6) | 0.0014 (5) | 0.0048 (5) | 0.0108 (5) |
C45 | 0.0236 (6) | 0.0321 (6) | 0.0366 (7) | 0.0031 (5) | 0.0058 (5) | 0.0240 (6) |
C46 | 0.0265 (7) | 0.0415 (7) | 0.0311 (7) | −0.0056 (6) | −0.0038 (6) | 0.0269 (6) |
C47 | 0.0394 (8) | 0.0381 (7) | 0.0183 (6) | −0.0062 (6) | 0.0004 (5) | 0.0146 (6) |
C48 | 0.0332 (7) | 0.0276 (6) | 0.0206 (6) | 0.0016 (5) | 0.0083 (5) | 0.0116 (5) |
O1—C8 | 1.2311 (13) | C25—H25A | 0.948 (15) |
N1—C7 | 1.2944 (14) | C25—H25B | 0.981 (16) |
N1—C6 | 1.3909 (14) | C25—H25C | 1.000 (16) |
N2—C8 | 1.3779 (14) | C26—C27 | 1.5159 (15) |
N2—C1 | 1.4004 (13) | C26—H26A | 0.983 (15) |
N2—C10 | 1.4711 (15) | C26—H26B | 0.988 (14) |
C1—C2 | 1.3986 (15) | C27—C28 | 1.3874 (17) |
C1—C6 | 1.4026 (15) | C27—C32 | 1.3939 (17) |
C2—C3 | 1.3843 (16) | C28—C29 | 1.3938 (16) |
C2—H2 | 0.976 (14) | C28—H28 | 0.990 (13) |
C3—C4 | 1.3908 (18) | C29—C30 | 1.3810 (19) |
C3—H3 | 1.002 (13) | C29—H29 | 0.996 (15) |
C4—C5 | 1.3793 (16) | C30—C31 | 1.383 (2) |
C4—H4 | 0.961 (13) | C30—H30 | 1.008 (14) |
C5—C6 | 1.4011 (15) | C31—C32 | 1.3954 (18) |
C5—H5 | 0.993 (14) | C31—H31 | 0.970 (16) |
C7—C8 | 1.4805 (16) | C32—H32 | 0.994 (16) |
C7—C9 | 1.4967 (15) | O3—C40 | 1.2259 (13) |
C9—H9A | 0.990 (18) | N5—C39 | 1.2892 (14) |
C9—H9B | 0.975 (16) | N5—C38 | 1.3926 (14) |
C9—H9C | 0.986 (16) | N6—C40 | 1.3798 (15) |
C10—C11 | 1.5148 (17) | N6—C33 | 1.3971 (14) |
C10—H10A | 0.986 (13) | N6—C42 | 1.4662 (14) |
C10—H10B | 1.012 (13) | C33—C38 | 1.4048 (15) |
C11—C16 | 1.3855 (17) | C33—C34 | 1.4053 (16) |
C11—C12 | 1.3982 (17) | C34—C35 | 1.3759 (17) |
C12—C13 | 1.3850 (18) | C34—H34 | 0.976 (14) |
C12—H12 | 0.999 (15) | C35—C36 | 1.3977 (18) |
C13—C14 | 1.383 (2) | C35—H35 | 0.940 (14) |
C13—H13 | 0.961 (16) | C36—C37 | 1.3772 (18) |
C14—C15 | 1.3821 (19) | C36—H36 | 0.971 (14) |
C14—H14 | 1.002 (14) | C37—C38 | 1.4012 (15) |
C15—C16 | 1.3917 (18) | C37—H37 | 0.972 (14) |
C15—H15 | 1.007 (16) | C39—C40 | 1.4828 (16) |
C16—H16 | 0.948 (14) | C39—C41 | 1.4927 (16) |
O2—C24 | 1.2267 (13) | C41—H41A | 0.990 (15) |
N3—C23 | 1.2965 (15) | C41—H41B | 0.985 (18) |
N3—C22 | 1.3942 (14) | C41—H41C | 0.979 (16) |
N4—C24 | 1.3854 (14) | C42—C43 | 1.5161 (17) |
N4—C17 | 1.3958 (14) | C42—H42A | 0.979 (13) |
N4—C26 | 1.4624 (14) | C42—H42B | 0.982 (15) |
C17—C22 | 1.4010 (15) | C43—C44 | 1.3888 (16) |
C17—C18 | 1.4051 (15) | C43—C48 | 1.3945 (16) |
C18—C19 | 1.3817 (16) | C44—C45 | 1.3884 (17) |
C18—H18 | 0.986 (14) | C44—H44 | 0.988 (13) |
C19—C20 | 1.3949 (17) | C45—C46 | 1.3825 (18) |
C19—H19 | 0.953 (13) | C45—H45 | 1.009 (14) |
C20—C21 | 1.3798 (17) | C46—C47 | 1.387 (2) |
C20—H20 | 0.962 (14) | C46—H46 | 0.946 (15) |
C21—C22 | 1.4018 (15) | C47—C48 | 1.3862 (19) |
C21—H21 | 0.992 (13) | C47—H47 | 0.954 (16) |
C23—C24 | 1.4801 (16) | C48—H48 | 0.991 (14) |
C23—C25 | 1.4924 (16) | ||
C7—N1—C6 | 118.37 (10) | C23—C25—H25B | 110.3 (9) |
C8—N2—C1 | 121.26 (9) | H25A—C25—H25B | 103.6 (12) |
C8—N2—C10 | 118.54 (9) | C23—C25—H25C | 110.7 (9) |
C1—N2—C10 | 120.15 (9) | H25A—C25—H25C | 106.7 (13) |
C2—C1—N2 | 122.24 (10) | H25B—C25—H25C | 114.0 (13) |
C2—C1—C6 | 119.46 (10) | N4—C26—C27 | 113.64 (10) |
N2—C1—C6 | 118.30 (9) | N4—C26—H26A | 106.3 (8) |
C3—C2—C1 | 119.68 (11) | C27—C26—H26A | 111.8 (8) |
C3—C2—H2 | 118.8 (8) | N4—C26—H26B | 108.7 (7) |
C1—C2—H2 | 121.5 (8) | C27—C26—H26B | 110.3 (7) |
C2—C3—C4 | 121.05 (11) | H26A—C26—H26B | 105.7 (11) |
C2—C3—H3 | 117.9 (7) | C28—C27—C32 | 119.23 (11) |
C4—C3—H3 | 121.1 (7) | C28—C27—C26 | 121.85 (10) |
C5—C4—C3 | 119.69 (10) | C32—C27—C26 | 118.89 (11) |
C5—C4—H4 | 120.1 (8) | C27—C28—C29 | 120.10 (12) |
C3—C4—H4 | 120.2 (8) | C27—C28—H28 | 119.8 (8) |
C4—C5—C6 | 120.25 (11) | C29—C28—H28 | 120.1 (8) |
C4—C5—H5 | 121.8 (8) | C30—C29—C28 | 120.69 (13) |
C6—C5—H5 | 118.0 (8) | C30—C29—H29 | 121.5 (8) |
N1—C6—C5 | 117.89 (10) | C28—C29—H29 | 117.8 (8) |
N1—C6—C1 | 122.23 (9) | C29—C30—C31 | 119.45 (11) |
C5—C6—C1 | 119.85 (10) | C29—C30—H30 | 120.6 (8) |
N1—C7—C8 | 123.90 (10) | C31—C30—H30 | 119.9 (8) |
N1—C7—C9 | 119.56 (10) | C30—C31—C32 | 120.36 (13) |
C8—C7—C9 | 116.53 (10) | C30—C31—H31 | 118.9 (10) |
O1—C8—N2 | 122.39 (10) | C32—C31—H31 | 120.8 (10) |
O1—C8—C7 | 121.74 (10) | C27—C32—C31 | 120.15 (13) |
N2—C8—C7 | 115.87 (9) | C27—C32—H32 | 119.6 (9) |
C7—C9—H9A | 110.1 (10) | C31—C32—H32 | 120.2 (9) |
C7—C9—H9B | 112.4 (9) | C39—N5—C38 | 118.69 (9) |
H9A—C9—H9B | 108.1 (13) | C40—N6—C33 | 121.90 (9) |
C7—C9—H9C | 110.8 (9) | C40—N6—C42 | 117.19 (9) |
H9A—C9—H9C | 106.8 (13) | C33—N6—C42 | 120.90 (10) |
H9B—C9—H9C | 108.4 (13) | N6—C33—C38 | 117.91 (10) |
N2—C10—C11 | 114.25 (10) | N6—C33—C34 | 122.53 (10) |
N2—C10—H10A | 108.4 (8) | C38—C33—C34 | 119.56 (10) |
C11—C10—H10A | 110.1 (8) | C35—C34—C33 | 119.27 (11) |
N2—C10—H10B | 105.3 (8) | C35—C34—H34 | 120.3 (8) |
C11—C10—H10B | 109.8 (8) | C33—C34—H34 | 120.4 (8) |
H10A—C10—H10B | 108.7 (11) | C34—C35—C36 | 121.73 (11) |
C16—C11—C12 | 119.09 (11) | C34—C35—H35 | 119.9 (8) |
C16—C11—C10 | 122.22 (11) | C36—C35—H35 | 118.4 (8) |
C12—C11—C10 | 118.65 (11) | C37—C36—C35 | 119.15 (11) |
C13—C12—C11 | 120.27 (13) | C37—C36—H36 | 121.2 (8) |
C13—C12—H12 | 120.0 (8) | C35—C36—H36 | 119.7 (8) |
C11—C12—H12 | 119.7 (8) | C36—C37—C38 | 120.58 (11) |
C14—C13—C12 | 120.42 (12) | C36—C37—H37 | 122.6 (8) |
C14—C13—H13 | 119.9 (9) | C38—C37—H37 | 116.8 (8) |
C12—C13—H13 | 119.7 (10) | N5—C38—C37 | 118.16 (10) |
C15—C14—C13 | 119.52 (12) | N5—C38—C33 | 122.14 (10) |
C15—C14—H14 | 118.7 (8) | C37—C38—C33 | 119.70 (10) |
C13—C14—H14 | 121.8 (8) | N5—C39—C40 | 123.91 (10) |
C14—C15—C16 | 120.50 (13) | N5—C39—C41 | 119.75 (10) |
C14—C15—H15 | 119.9 (9) | C40—C39—C41 | 116.33 (10) |
C16—C15—H15 | 119.5 (9) | O3—C40—N6 | 122.49 (10) |
C11—C16—C15 | 120.20 (12) | O3—C40—C39 | 122.08 (11) |
C11—C16—H16 | 120.5 (9) | N6—C40—C39 | 115.43 (9) |
C15—C16—H16 | 119.3 (9) | C39—C41—H41A | 111.6 (9) |
C23—N3—C22 | 118.48 (10) | C39—C41—H41B | 110.4 (9) |
C24—N4—C17 | 121.54 (9) | H41A—C41—H41B | 105.6 (13) |
C24—N4—C26 | 117.97 (9) | C39—C41—H41C | 110.2 (9) |
C17—N4—C26 | 120.49 (9) | H41A—C41—H41C | 108.9 (12) |
N4—C17—C22 | 118.35 (9) | H41B—C41—H41C | 110.0 (13) |
N4—C17—C18 | 122.32 (10) | N6—C42—C43 | 113.72 (9) |
C22—C17—C18 | 119.33 (10) | N6—C42—H42A | 106.6 (8) |
C19—C18—C17 | 120.09 (11) | C43—C42—H42A | 110.5 (8) |
C19—C18—H18 | 121.4 (8) | N6—C42—H42B | 110.3 (8) |
C17—C18—H18 | 118.5 (8) | C43—C42—H42B | 109.3 (8) |
C18—C19—C20 | 120.62 (11) | H42A—C42—H42B | 106.1 (11) |
C18—C19—H19 | 117.1 (8) | C44—C43—C48 | 118.65 (11) |
C20—C19—H19 | 122.2 (8) | C44—C43—C42 | 122.39 (10) |
C21—C20—C19 | 119.71 (11) | C48—C43—C42 | 118.95 (10) |
C21—C20—H20 | 122.0 (8) | C45—C44—C43 | 120.77 (11) |
C19—C20—H20 | 118.3 (8) | C45—C44—H44 | 119.1 (8) |
C20—C21—C22 | 120.58 (11) | C43—C44—H44 | 120.1 (8) |
C20—C21—H21 | 119.9 (8) | C46—C45—C44 | 120.23 (12) |
C22—C21—H21 | 119.5 (8) | C46—C45—H45 | 119.7 (8) |
N3—C22—C17 | 122.10 (10) | C44—C45—H45 | 120.1 (8) |
N3—C22—C21 | 118.25 (10) | C45—C46—C47 | 119.48 (12) |
C17—C22—C21 | 119.64 (10) | C45—C46—H46 | 119.7 (9) |
N3—C23—C24 | 123.92 (10) | C47—C46—H46 | 120.8 (9) |
N3—C23—C25 | 119.38 (11) | C48—C47—C46 | 120.36 (12) |
C24—C23—C25 | 116.70 (10) | C48—C47—H47 | 119.4 (10) |
O2—C24—N4 | 122.12 (10) | C46—C47—H47 | 120.3 (10) |
O2—C24—C23 | 122.44 (10) | C47—C48—C43 | 120.50 (12) |
N4—C24—C23 | 115.43 (9) | C47—C48—H48 | 118.3 (8) |
C23—C25—H25A | 111.4 (9) | C43—C48—H48 | 121.2 (8) |
C8—N2—C1—C2 | 178.23 (10) | C26—N4—C24—O2 | 4.31 (15) |
C10—N2—C1—C2 | −4.42 (16) | C17—N4—C24—C23 | 5.08 (14) |
C8—N2—C1—C6 | −1.61 (15) | C26—N4—C24—C23 | −174.92 (9) |
C10—N2—C1—C6 | 175.74 (10) | N3—C23—C24—O2 | 177.27 (10) |
N2—C1—C2—C3 | 179.07 (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—N4 | 175.95 (9) |
C2—C3—C4—C5 | 1.10 (17) | C24—N4—C26—C27 | −103.32 (11) |
C3—C4—C5—C6 | −0.87 (17) | C17—N4—C26—C27 | 76.68 (13) |
C7—N1—C6—C5 | 179.64 (10) | N4—C26—C27—C28 | 17.37 (15) |
C7—N1—C6—C1 | 1.57 (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—C29 | 177.52 (10) |
C2—C1—C6—N1 | 179.34 (10) | C27—C28—C29—C30 | −0.45 (17) |
N2—C1—C6—N1 | −0.82 (15) | C28—C29—C30—C31 | 0.80 (19) |
C2—C1—C6—C5 | 1.31 (16) | C29—C30—C31—C32 | −0.1 (2) |
N2—C1—C6—C5 | −178.85 (9) | C28—C27—C32—C31 | 1.25 (19) |
C6—N1—C7—C8 | 0.03 (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—C38 | 1.53 (16) |
C10—N2—C8—O1 | 4.66 (16) | C42—N6—C33—C38 | −178.70 (10) |
C1—N2—C8—C7 | 3.00 (15) | C40—N6—C33—C34 | −178.52 (10) |
C10—N2—C8—C7 | −174.40 (9) | C42—N6—C33—C34 | 1.26 (16) |
N1—C7—C8—O1 | 178.65 (10) | N6—C33—C34—C35 | −179.09 (10) |
C9—C7—C8—O1 | −2.92 (16) | C38—C33—C34—C35 | 0.86 (17) |
N1—C7—C8—N2 | −2.28 (16) | C33—C34—C35—C36 | 0.26 (18) |
C9—C7—C8—N2 | 176.14 (10) | C34—C35—C36—C37 | −1.00 (18) |
C8—N2—C10—C11 | −106.81 (11) | C35—C36—C37—C38 | 0.59 (18) |
C1—N2—C10—C11 | 75.76 (13) | C39—N5—C38—C37 | −179.68 (10) |
N2—C10—C11—C16 | 22.47 (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—C33 | 0.52 (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—N5 | 179.20 (10) |
C12—C13—C14—C15 | 0.80 (18) | N6—C33—C38—C37 | 178.71 (10) |
C13—C14—C15—C16 | −0.69 (18) | C34—C33—C38—C37 | −1.25 (16) |
C12—C11—C16—C15 | 0.61 (17) | C38—N5—C39—C40 | 0.46 (16) |
C10—C11—C16—C15 | 178.37 (11) | C38—N5—C39—C41 | −179.43 (10) |
C14—C15—C16—C11 | −0.01 (18) | C33—N6—C40—O3 | 178.91 (10) |
C24—N4—C17—C22 | −3.62 (15) | C42—N6—C40—O3 | −0.87 (16) |
C26—N4—C17—C22 | 176.38 (9) | C33—N6—C40—C39 | −1.20 (15) |
C24—N4—C17—C18 | 176.43 (9) | C42—N6—C40—C39 | 179.02 (10) |
C26—N4—C17—C18 | −3.57 (15) | N5—C39—C40—O3 | −179.93 (11) |
N4—C17—C18—C19 | 179.35 (9) | C41—C39—C40—O3 | −0.04 (16) |
C22—C17—C18—C19 | −0.61 (15) | N5—C39—C40—N6 | 0.18 (16) |
C17—C18—C19—C20 | −0.74 (16) | C41—C39—C40—N6 | −179.92 (10) |
C18—C19—C20—C21 | 1.39 (16) | C40—N6—C42—C43 | 97.49 (12) |
C19—C20—C21—C22 | −0.67 (16) | C33—N6—C42—C43 | −82.29 (13) |
C23—N3—C22—C17 | 1.47 (15) | N6—C42—C43—C44 | 3.16 (17) |
C23—N3—C22—C21 | −179.74 (9) | N6—C42—C43—C48 | −176.14 (11) |
N4—C17—C22—N3 | 0.13 (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—C46 | 1.09 (18) |
C18—C17—C22—C21 | 1.31 (15) | C44—C45—C46—C47 | −0.87 (18) |
C20—C21—C22—N3 | −179.50 (10) | C45—C46—C47—C48 | 0.01 (19) |
C20—C21—C22—C17 | −0.68 (16) | C46—C47—C48—C43 | 0.64 (19) |
C22—N3—C23—C24 | 0.29 (15) | C44—C43—C48—C47 | −0.42 (18) |
C22—N3—C23—C25 | −179.15 (10) | C42—C43—C48—C47 | 178.91 (12) |
C17—N4—C24—O2 | −175.69 (9) |
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. |
Acknowledgements
JTM thanks Tulane University for support of the Tulane Crystallography Laboratory.
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