organic compounds
2-{3-[2-(2-Chlorophenyl)ethyl]-2-oxo-1,2-dihydroquinoxalin-1-yl}acetohydrazide
aLaboratory of Medicinal Chemistry, Faculty of Medicine and Pharmacy, Mohammed V University, Rabat, Morocco, bLaboratory of Agrophysiology, Biotechnology, Environnement and Quality, Faculty of Science, Ibn Tofail University, Kenitra, Morocco, cLaboratoire de Chimie Organique Heterocyclique URAC 21, Av. Ibn Battouta, BP 1014, Faculte des Sciences, Universite Mohammed V, Rabat, Morocco, and dDepartment of Chemistry, Tulane University, New Orleans, LA 70118, USA
*Correspondence e-mail: mohcinemissioui@yahoo.com
In the title compound, C18H17ClN4O2, the dihydroquinoxaline moiety deviates slightly from planarity. The benzene ring and its chloro and methylene substituents are disordered over two sets of sites, with an occupancy ratio of 0.675 (3):0.325 (3). In the crystal, corrugated sheets parallel to (100) are formed by N—H⋯O, N—H⋯Cl and N—H⋯N hydrogen bonds. The structure was refined as a two-component inversion twin.
Keywords: crystal structure; quinoxaline; hydrazide; hydrogen bond.
CCDC reference: 1577756
Structure description
Among the various classes of nitrogen et al., 2014). Some analogs have been synthesized and evaluated for their antimicrobial activity and many possess diverse biological activities including insecticidal, fungicidal, herbicidal, anthelmintic and antiviral (Ramli & Essassi, 2015). As a continuation of our work on the development of N-substituted quinoxaline-2-one derivatives in order to evaluate their pharmacological activity, we have studied the condensation reaction of ethyl 2-[3-(2-chlorophenethyl)-2-oxoquinoxalin-1(2H)-yl]acetate with hydrazine hydrate in ethanol to form the title compound (Fig. 1) in good yield (Ramli et al., 2011, 2013; Caleb et al., 2016).
quinoxaline derivatives display a broad spectrum of biological activities (RamliThe bicyclic core of the title compound is not quite planar, as indicated by the dihedral angle of 1.52 (16)° between the pyrazinone and the benzene rings. The pyrazinone ring is inclined to the major disorder component of the chlorophenyl ring by 24.80 (19)°. In the crystal, the molecules form zigzag chains running along the c-axis direction through N4—H4A⋯N2 hydrogen bonds together with weak N4—H4B⋯Cl1 interactions (Table 1 and Fig. 2). N3—H3A⋯O2 hydrogen bonds form chains along b (Table 1 and Fig. 2) and combine with the sheets shown in Fig. 3 to form corrugated sheets parallel to (100).
Synthesis and crystallization
To a solution of ethyl 2-[3-(2-chlorophenethyl)-2-oxoquinoxalin-1(2H)-yl]acetate (2.70 mmol, 1 g) in 20 ml of ethanol, hydrazine hydrate (4.58 mmol, 229.49 mg) was added. The mixture was stirred at room temperature for 24 h. The solid material was removed by filtration and the solvent evaporated under vacuum. The solid product was purified by recrystallization from ethanol solution to afford colorless block-like crystals of the title compound (yield 63%).
Refinement
Crystal and . The 2-chlorobenzyl group is disordered over several closely spaced positions. After several attempts, the only feasible model was a two-site one, treating the rings as rigid hexagons. The structure was refined as a two-component inversion twin.
details are presented in Table 2Structural data
CCDC reference: 1577756
https://doi.org/10.1107/S2414314617014249/sj4138sup1.cif
contains datablocks global, I. DOI:Structure factors: contains datablock I. DOI: https://doi.org/10.1107/S2414314617014249/sj4138Isup2.hkl
Supporting information file. DOI: https://doi.org/10.1107/S2414314617014249/sj4138Isup3.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: SHELXL2014 (Sheldrick, 2015b); molecular graphics: DIAMOND (Brandenburg & Putz, 2012); software used to prepare material for publication: SHELXTL (Sheldrick, 2008).C18H17ClN4O2 | Dx = 1.423 Mg m−3 |
Mr = 356.80 | Mo Kα radiation, λ = 0.71073 Å |
Orthorhombic, Pna21 | Cell parameters from 6865 reflections |
a = 24.258 (3) Å | θ = 2.2–27.5° |
b = 4.6484 (5) Å | µ = 0.25 mm−1 |
c = 14.7708 (16) Å | T = 100 K |
V = 1665.6 (3) Å3 | Block, colorless |
Z = 4 | 0.25 × 0.16 × 0.05 mm |
F(000) = 744 |
Bruker SMART APEX CCD diffractometer | 4036 independent reflections |
Radiation source: fine-focus sealed tube | 3379 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.027 |
Detector resolution: 8.3333 pixels mm-1 | θmax = 28.3°, θmin = 1.7° |
ω scans | h = −32→32 |
Absorption correction: multi-scan (SADABS; Bruker, 2016) | k = −6→6 |
Tmin = 0.94, Tmax = 0.99 | l = −19→19 |
7372 measured reflections |
Refinement on F2 | Secondary atom site location: difference Fourier map |
Least-squares matrix: full | Hydrogen site location: mixed |
R[F2 > 2σ(F2)] = 0.052 | H atoms treated by a mixture of independent and constrained refinement |
wR(F2) = 0.145 | w = 1/[σ2(Fo2) + (0.0818P)2 + 0.3986P] where P = (Fo2 + 2Fc2)/3 |
S = 1.07 | (Δ/σ)max < 0.001 |
4036 reflections | Δρmax = 0.77 e Å−3 |
231 parameters | Δρmin = −0.30 e Å−3 |
84 restraints | Absolute structure: Refined as an inversion twin |
Primary atom site location: structure-invariant direct methods | Absolute structure parameter: 0.49 (16) |
Experimental. The diffraction data were collected in three sets of 363 frames (0.5° width in ω) at φ = 0, 120 and 240°. A scan time of 180 sec/frame was used. |
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. The 2-chlorobenzyl group is disordered over several closely spaced positions. After several attempts, the only feasible model was a 2-site one treating the rings as rigid hexagons. H-atoms attached to carbon were placed in idealized positions while those attached to nitrogen were placed in locations derived from a difference map and their coordinates adjusted to give N—H = 0.91 %A. All were included as riding contributions. Refined as a 2-component inversion twin. |
x | y | z | Uiso*/Ueq | Occ. (<1) | |
O1 | 0.57433 (10) | 0.7964 (6) | 0.42015 (17) | 0.0305 (6) | |
O2 | 0.43551 (10) | 0.6782 (5) | 0.38490 (17) | 0.0267 (5) | |
N1 | 0.50239 (11) | 0.8913 (6) | 0.51467 (18) | 0.0231 (6) | |
N2 | 0.54455 (12) | 0.4766 (6) | 0.63241 (19) | 0.0242 (6) | |
N3 | 0.41985 (12) | 1.1092 (6) | 0.3195 (2) | 0.0263 (6) | |
H3A | 0.4245 | 1.3014 | 0.3283 | 0.034 (11)* | |
N4 | 0.38670 (13) | 0.9972 (7) | 0.2490 (2) | 0.0317 (7) | |
H4A | 0.4043 | 0.8569 | 0.2173 | 0.044 (13)* | |
H4B | 0.3559 | 0.9345 | 0.2781 | 0.038 (12)* | |
C1 | 0.49487 (13) | 0.6127 (7) | 0.6508 (2) | 0.0233 (6) | |
C2 | 0.46541 (15) | 0.5374 (8) | 0.7293 (2) | 0.0293 (7) | |
H2 | 0.4799 | 0.3950 | 0.7688 | 0.035* | |
C3 | 0.41607 (16) | 0.6664 (9) | 0.7498 (2) | 0.0339 (8) | |
H3 | 0.3969 | 0.6161 | 0.8036 | 0.041* | |
C4 | 0.39449 (15) | 0.8702 (9) | 0.6914 (3) | 0.0374 (9) | |
H4 | 0.3602 | 0.9581 | 0.7056 | 0.045* | |
C5 | 0.42163 (15) | 0.9485 (8) | 0.6132 (3) | 0.0312 (8) | |
H5 | 0.4059 | 1.0881 | 0.5740 | 0.037* | |
C6 | 0.47239 (14) | 0.8223 (7) | 0.5917 (2) | 0.0234 (7) | |
C7 | 0.55016 (14) | 0.7508 (7) | 0.4917 (2) | 0.0234 (6) | |
C8 | 0.57052 (13) | 0.5406 (7) | 0.5594 (2) | 0.0237 (7) | |
C9 | 0.48067 (14) | 1.0949 (7) | 0.4481 (2) | 0.0246 (7) | |
H9A | 0.5116 | 1.1848 | 0.4147 | 0.030* | |
H9B | 0.4600 | 1.2491 | 0.4795 | 0.030* | |
C10 | 0.44243 (13) | 0.9402 (7) | 0.3812 (2) | 0.0215 (6) | |
C11 | 0.62385 (13) | 0.3913 (7) | 0.5368 (2) | 0.0261 (7) | |
H11A | 0.6205 | 0.3004 | 0.4764 | 0.031* | |
H11B | 0.6305 | 0.2368 | 0.5816 | 0.031* | |
Cl1 | 0.74190 (7) | 0.3151 (6) | 0.69305 (14) | 0.0692 (6) | 0.675 (3) |
C12 | 0.6744 (3) | 0.6004 (17) | 0.5363 (5) | 0.0297 (18) | 0.675 (3) |
H12A | 0.6689 | 0.7525 | 0.4903 | 0.036* | 0.675 (3) |
H12B | 0.6783 | 0.6934 | 0.5963 | 0.036* | 0.675 (3) |
C13 | 0.72605 (16) | 0.4260 (10) | 0.5144 (3) | 0.0332 (14) | 0.675 (3) |
C14 | 0.75662 (17) | 0.2843 (10) | 0.5803 (3) | 0.0384 (14) | 0.675 (3) |
C15 | 0.80138 (15) | 0.1150 (10) | 0.5555 (4) | 0.0494 (16) | 0.675 (3) |
H15 | 0.8223 | 0.0182 | 0.6005 | 0.059* | 0.675 (3) |
C16 | 0.81556 (16) | 0.0875 (11) | 0.4647 (4) | 0.054 (2) | 0.675 (3) |
H16 | 0.8462 | −0.0281 | 0.4477 | 0.065* | 0.675 (3) |
C17 | 0.7850 (2) | 0.2293 (13) | 0.3988 (3) | 0.061 (2) | 0.675 (3) |
H17 | 0.7947 | 0.2105 | 0.3367 | 0.073* | 0.675 (3) |
C18 | 0.7402 (2) | 0.3985 (12) | 0.4236 (3) | 0.0528 (18) | 0.675 (3) |
H18 | 0.7193 | 0.4953 | 0.3786 | 0.063* | 0.675 (3) |
Cl1A | 0.71901 (15) | 0.5143 (12) | 0.3615 (3) | 0.0692 (6) | 0.325 (3) |
C12A | 0.6753 (6) | 0.566 (4) | 0.5630 (14) | 0.0297 (18) | 0.325 (3) |
H12C | 0.6766 | 0.7474 | 0.5279 | 0.036* | 0.325 (3) |
H12D | 0.6742 | 0.6146 | 0.6282 | 0.036* | 0.325 (3) |
C13A | 0.7262 (4) | 0.383 (2) | 0.5423 (8) | 0.0332 (14) | 0.325 (3) |
C14A | 0.7474 (4) | 0.345 (2) | 0.4556 (7) | 0.0384 (14) | 0.325 (3) |
C15A | 0.7933 (4) | 0.171 (2) | 0.4423 (6) | 0.0494 (16) | 0.325 (3) |
H15A | 0.8077 | 0.1451 | 0.3830 | 0.059* | 0.325 (3) |
C16A | 0.8180 (4) | 0.035 (2) | 0.5155 (8) | 0.054 (2) | 0.325 (3) |
H16A | 0.8494 | −0.0840 | 0.5064 | 0.065* | 0.325 (3) |
C17A | 0.7969 (4) | 0.073 (3) | 0.6022 (7) | 0.061 (2) | 0.325 (3) |
H17A | 0.8138 | −0.0203 | 0.6523 | 0.073* | 0.325 (3) |
C18A | 0.7510 (5) | 0.247 (3) | 0.6156 (6) | 0.0528 (18) | 0.325 (3) |
H18A | 0.7365 | 0.2725 | 0.6748 | 0.063* | 0.325 (3) |
U11 | U22 | U33 | U12 | U13 | U23 | |
O1 | 0.0359 (13) | 0.0295 (13) | 0.0259 (12) | −0.0008 (10) | 0.0010 (10) | 0.0006 (10) |
O2 | 0.0348 (12) | 0.0148 (10) | 0.0304 (12) | −0.0028 (9) | −0.0054 (10) | 0.0007 (9) |
N1 | 0.0264 (13) | 0.0183 (12) | 0.0245 (13) | −0.0020 (11) | −0.0054 (11) | −0.0004 (11) |
N2 | 0.0259 (13) | 0.0234 (14) | 0.0232 (13) | 0.0003 (11) | −0.0059 (11) | −0.0006 (11) |
N3 | 0.0324 (14) | 0.0174 (13) | 0.0292 (15) | −0.0031 (11) | −0.0085 (11) | 0.0012 (11) |
N4 | 0.0362 (16) | 0.0261 (15) | 0.0328 (16) | −0.0027 (13) | −0.0106 (13) | −0.0001 (12) |
C1 | 0.0261 (15) | 0.0233 (15) | 0.0204 (14) | −0.0009 (12) | −0.0041 (12) | −0.0023 (12) |
C2 | 0.0308 (18) | 0.0328 (18) | 0.0244 (16) | −0.0013 (14) | −0.0047 (13) | 0.0016 (15) |
C3 | 0.0319 (18) | 0.045 (2) | 0.0244 (17) | −0.0014 (16) | 0.0015 (14) | −0.0027 (16) |
C4 | 0.0275 (17) | 0.043 (2) | 0.042 (2) | 0.0081 (16) | 0.0027 (15) | −0.0094 (18) |
C5 | 0.0309 (18) | 0.0278 (19) | 0.0349 (19) | 0.0032 (14) | −0.0048 (14) | 0.0001 (14) |
C6 | 0.0278 (16) | 0.0187 (15) | 0.0237 (15) | −0.0005 (12) | −0.0061 (12) | −0.0018 (12) |
C7 | 0.0272 (16) | 0.0187 (15) | 0.0243 (15) | −0.0028 (12) | −0.0031 (11) | −0.0032 (12) |
C8 | 0.0227 (15) | 0.0202 (15) | 0.0281 (16) | −0.0022 (12) | −0.0061 (12) | −0.0025 (13) |
C9 | 0.0303 (16) | 0.0157 (15) | 0.0278 (16) | 0.0013 (13) | −0.0063 (12) | 0.0034 (12) |
C10 | 0.0248 (14) | 0.0176 (15) | 0.0221 (14) | −0.0005 (11) | 0.0016 (12) | −0.0009 (12) |
C11 | 0.0271 (15) | 0.0237 (16) | 0.0276 (16) | 0.0028 (13) | −0.0033 (13) | −0.0019 (13) |
Cl1 | 0.0429 (8) | 0.1067 (17) | 0.0581 (9) | −0.0183 (9) | −0.0076 (7) | 0.0194 (11) |
C12 | 0.0289 (18) | 0.025 (3) | 0.036 (5) | 0.0000 (18) | −0.001 (3) | 0.000 (3) |
C13 | 0.0282 (18) | 0.026 (2) | 0.045 (4) | −0.0052 (17) | 0.005 (2) | −0.004 (3) |
C14 | 0.023 (2) | 0.035 (3) | 0.057 (4) | −0.004 (2) | 0.001 (2) | 0.003 (3) |
C15 | 0.023 (2) | 0.040 (3) | 0.085 (4) | −0.003 (2) | 0.000 (3) | 0.002 (3) |
C16 | 0.033 (2) | 0.043 (3) | 0.086 (6) | −0.004 (2) | 0.017 (4) | −0.023 (4) |
C17 | 0.051 (3) | 0.062 (4) | 0.068 (4) | −0.015 (3) | 0.019 (3) | −0.014 (3) |
C18 | 0.043 (3) | 0.053 (4) | 0.062 (4) | −0.011 (3) | 0.005 (3) | −0.001 (3) |
Cl1A | 0.0429 (8) | 0.1067 (17) | 0.0581 (9) | −0.0183 (9) | −0.0076 (7) | 0.0194 (11) |
C12A | 0.0289 (18) | 0.025 (3) | 0.036 (5) | 0.0000 (18) | −0.001 (3) | 0.000 (3) |
C13A | 0.0282 (18) | 0.026 (2) | 0.045 (4) | −0.0052 (17) | 0.005 (2) | −0.004 (3) |
C14A | 0.023 (2) | 0.035 (3) | 0.057 (4) | −0.004 (2) | 0.001 (2) | 0.003 (3) |
C15A | 0.023 (2) | 0.040 (3) | 0.085 (4) | −0.003 (2) | 0.000 (3) | 0.002 (3) |
C16A | 0.033 (2) | 0.043 (3) | 0.086 (6) | −0.004 (2) | 0.017 (4) | −0.023 (4) |
C17A | 0.051 (3) | 0.062 (4) | 0.068 (4) | −0.015 (3) | 0.019 (3) | −0.014 (3) |
C18A | 0.043 (3) | 0.053 (4) | 0.062 (4) | −0.011 (3) | 0.005 (3) | −0.001 (3) |
O1—C7 | 1.227 (4) | C11—H11B | 0.9900 |
O2—C10 | 1.231 (4) | Cl1—C14 | 1.709 (4) |
N1—C7 | 1.373 (4) | C12—C13 | 1.528 (8) |
N1—C6 | 1.389 (4) | C12—H12A | 0.9900 |
N1—C9 | 1.463 (4) | C12—H12B | 0.9900 |
N2—C8 | 1.284 (5) | C13—C14 | 1.3900 |
N2—C1 | 1.388 (4) | C13—C18 | 1.3900 |
N3—C10 | 1.323 (4) | C14—C15 | 1.3900 |
N3—N4 | 1.414 (4) | C15—C16 | 1.3900 |
N3—H3A | 0.9099 | C15—H15 | 0.9500 |
N4—H4A | 0.9100 | C16—C17 | 1.3900 |
N4—H4B | 0.9100 | C16—H16 | 0.9500 |
C1—C2 | 1.407 (5) | C17—C18 | 1.3900 |
C1—C6 | 1.416 (4) | C17—H17 | 0.9500 |
C2—C3 | 1.372 (5) | C18—H18 | 0.9500 |
C2—H2 | 0.9500 | Cl1A—C14A | 1.740 (9) |
C3—C4 | 1.384 (6) | C12A—C13A | 1.533 (18) |
C3—H3 | 0.9500 | C12A—H12C | 0.9900 |
C4—C5 | 1.378 (6) | C12A—H12D | 0.9900 |
C4—H4 | 0.9500 | C13A—C14A | 1.3900 |
C5—C6 | 1.401 (5) | C13A—C18A | 1.3900 |
C5—H5 | 0.9500 | C14A—C15A | 1.3900 |
C7—C8 | 1.483 (5) | C15A—C16A | 1.3900 |
C8—C11 | 1.506 (4) | C15A—H15A | 0.9500 |
C9—C10 | 1.533 (4) | C16A—C17A | 1.3900 |
C9—H9A | 0.9900 | C16A—H16A | 0.9500 |
C9—H9B | 0.9900 | C17A—C18A | 1.3900 |
C11—C12A | 1.538 (16) | C17A—H17A | 0.9500 |
C11—C12 | 1.564 (8) | C18A—H18A | 0.9500 |
C11—H11A | 0.9900 | ||
C7—N1—C6 | 122.4 (3) | H11A—C11—H11B | 107.8 |
C7—N1—C9 | 116.4 (3) | C13—C12—C11 | 108.3 (5) |
C6—N1—C9 | 120.8 (3) | C13—C12—H12A | 110.0 |
C8—N2—C1 | 119.0 (3) | C11—C12—H12A | 110.0 |
C10—N3—N4 | 121.6 (3) | C13—C12—H12B | 110.0 |
C10—N3—H3A | 115.7 | C11—C12—H12B | 110.0 |
N4—N3—H3A | 122.5 | H12A—C12—H12B | 108.4 |
N3—N4—H4A | 112.1 | C14—C13—C18 | 120.0 |
N3—N4—H4B | 103.7 | C14—C13—C12 | 122.7 (4) |
H4A—N4—H4B | 113.5 | C18—C13—C12 | 117.2 (4) |
N2—C1—C2 | 119.2 (3) | C15—C14—C13 | 120.0 |
N2—C1—C6 | 121.8 (3) | C15—C14—Cl1 | 117.9 (3) |
C2—C1—C6 | 118.9 (3) | C13—C14—Cl1 | 122.1 (3) |
C3—C2—C1 | 121.0 (3) | C14—C15—C16 | 120.0 |
C3—C2—H2 | 119.5 | C14—C15—H15 | 120.0 |
C1—C2—H2 | 119.5 | C16—C15—H15 | 120.0 |
C2—C3—C4 | 119.5 (3) | C17—C16—C15 | 120.0 |
C2—C3—H3 | 120.3 | C17—C16—H16 | 120.0 |
C4—C3—H3 | 120.3 | C15—C16—H16 | 120.0 |
C5—C4—C3 | 121.5 (3) | C16—C17—C18 | 120.0 |
C5—C4—H4 | 119.3 | C16—C17—H17 | 120.0 |
C3—C4—H4 | 119.3 | C18—C17—H17 | 120.0 |
C4—C5—C6 | 120.0 (3) | C17—C18—C13 | 120.0 |
C4—C5—H5 | 120.0 | C17—C18—H18 | 120.0 |
C6—C5—H5 | 120.0 | C13—C18—H18 | 120.0 |
N1—C6—C5 | 123.4 (3) | C13A—C12A—C11 | 108.1 (11) |
N1—C6—C1 | 117.5 (3) | C13A—C12A—H12C | 110.1 |
C5—C6—C1 | 119.1 (3) | C11—C12A—H12C | 110.1 |
O1—C7—N1 | 122.3 (3) | C13A—C12A—H12D | 110.1 |
O1—C7—C8 | 122.4 (3) | C11—C12A—H12D | 110.1 |
N1—C7—C8 | 115.3 (3) | H12C—C12A—H12D | 108.4 |
N2—C8—C7 | 123.8 (3) | C14A—C13A—C18A | 120.0 |
N2—C8—C11 | 120.1 (3) | C14A—C13A—C12A | 123.5 (10) |
C7—C8—C11 | 116.1 (3) | C18A—C13A—C12A | 116.5 (10) |
N1—C9—C10 | 110.3 (3) | C15A—C14A—C13A | 120.0 |
N1—C9—H9A | 109.6 | C15A—C14A—Cl1A | 117.8 (6) |
C10—C9—H9A | 109.6 | C13A—C14A—Cl1A | 122.2 (6) |
N1—C9—H9B | 109.6 | C14A—C15A—C16A | 120.0 |
C10—C9—H9B | 109.6 | C14A—C15A—H15A | 120.0 |
H9A—C9—H9B | 108.1 | C16A—C15A—H15A | 120.0 |
O2—C10—N3 | 124.2 (3) | C15A—C16A—C17A | 120.0 |
O2—C10—C9 | 121.2 (3) | C15A—C16A—H16A | 120.0 |
N3—C10—C9 | 114.6 (3) | C17A—C16A—H16A | 120.0 |
C8—C11—C12A | 113.4 (8) | C18A—C17A—C16A | 120.0 |
C8—C11—C12 | 112.8 (4) | C18A—C17A—H17A | 120.0 |
C8—C11—H11A | 109.0 | C16A—C17A—H17A | 120.0 |
C12—C11—H11A | 109.0 | C17A—C18A—C13A | 120.0 |
C8—C11—H11B | 109.0 | C17A—C18A—H18A | 120.0 |
C12—C11—H11B | 109.0 | C13A—C18A—H18A | 120.0 |
C8—N2—C1—C2 | 178.2 (3) | N2—C8—C11—C12A | −97.9 (9) |
C8—N2—C1—C6 | −0.7 (5) | C7—C8—C11—C12A | 84.3 (9) |
N2—C1—C2—C3 | −179.8 (3) | N2—C8—C11—C12 | −115.1 (4) |
C6—C1—C2—C3 | −0.9 (5) | C7—C8—C11—C12 | 67.1 (4) |
C1—C2—C3—C4 | 1.1 (6) | C8—C11—C12—C13 | 179.0 (4) |
C2—C3—C4—C5 | −0.4 (6) | C11—C12—C13—C14 | −86.4 (5) |
C3—C4—C5—C6 | −0.4 (6) | C11—C12—C13—C18 | 89.8 (4) |
C7—N1—C6—C5 | −175.4 (3) | C18—C13—C14—C15 | 0.0 |
C9—N1—C6—C5 | −3.0 (5) | C12—C13—C14—C15 | 176.2 (5) |
C7—N1—C6—C1 | 4.5 (4) | C18—C13—C14—Cl1 | 178.8 (4) |
C9—N1—C6—C1 | 176.9 (3) | C12—C13—C14—Cl1 | −5.0 (5) |
C4—C5—C6—N1 | −179.5 (3) | C13—C14—C15—C16 | 0.0 |
C4—C5—C6—C1 | 0.6 (5) | Cl1—C14—C15—C16 | −178.9 (4) |
N2—C1—C6—N1 | −1.0 (5) | C14—C15—C16—C17 | 0.0 |
C2—C1—C6—N1 | −179.8 (3) | C15—C16—C17—C18 | 0.0 |
N2—C1—C6—C5 | 178.9 (3) | C16—C17—C18—C13 | 0.0 |
C2—C1—C6—C5 | 0.1 (5) | C14—C13—C18—C17 | 0.0 |
C6—N1—C7—O1 | 174.3 (3) | C12—C13—C18—C17 | −176.4 (4) |
C9—N1—C7—O1 | 1.6 (5) | C8—C11—C12A—C13A | 176.3 (8) |
C6—N1—C7—C8 | −5.9 (4) | C11—C12A—C13A—C14A | 77.5 (13) |
C9—N1—C7—C8 | −178.6 (3) | C11—C12A—C13A—C18A | −101.4 (12) |
C1—N2—C8—C7 | −1.0 (5) | C18A—C13A—C14A—C15A | 0.0 |
C1—N2—C8—C11 | −178.6 (3) | C12A—C13A—C14A—C15A | −178.9 (9) |
O1—C7—C8—N2 | −176.0 (3) | C18A—C13A—C14A—Cl1A | −178.8 (9) |
N1—C7—C8—N2 | 4.2 (5) | C12A—C13A—C14A—Cl1A | 2.3 (11) |
O1—C7—C8—C11 | 1.8 (4) | C13A—C14A—C15A—C16A | 0.0 |
N1—C7—C8—C11 | −178.1 (3) | Cl1A—C14A—C15A—C16A | 178.9 (8) |
C7—N1—C9—C10 | 88.2 (3) | C14A—C15A—C16A—C17A | 0.0 |
C6—N1—C9—C10 | −84.6 (3) | C15A—C16A—C17A—C18A | 0.0 |
N4—N3—C10—O2 | −2.4 (5) | C16A—C17A—C18A—C13A | 0.0 |
N4—N3—C10—C9 | 175.5 (3) | C14A—C13A—C18A—C17A | 0.0 |
N1—C9—C10—O2 | −3.5 (4) | C12A—C13A—C18A—C17A | 179.0 (8) |
N1—C9—C10—N3 | 178.6 (3) |
D—H···A | D—H | H···A | D···A | D—H···A |
N3—H3A···O2i | 0.91 | 1.96 | 2.842 (4) | 163 |
N4—H4A···N2ii | 0.91 | 2.35 | 3.256 (4) | 175 |
N4—H4B···Cl1ii | 0.91 | 2.92 | 3.539 (3) | 126 |
Symmetry codes: (i) x, y+1, z; (ii) −x+1, −y+1, z−1/2. |
Acknowledgements
JTM thanks Tulane University for support of the Tulane Crystallography Laboratory.
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