organic compounds
1-[(Oxiran-2-yl)methyl]-3-phenyl-1,2-dihydroquinoxalin-2-one
aLaboratoire 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, bLaboratory of Medicinal Chemistry, Faculty of Medicine and Pharmacy, University Mohammed V, Rabat, Morocco, and cDepartment of Chemistry, Tulane University, New Orleans, LA 70118, USA
*Correspondence e-mail: ab.nadeem2018@gmail.com
The 17H14N2O2, consists of two independent molecules differing mainly in the orientations of the phenyl and oxirane substituents. In the first molecule, the dihedral angle between the dihydroquinoxaline ring system and phenyl ring is 28.4 (2)° and the N—C—C—O torsion angle is 87.8 (5)°; corresponding data for the second molecule are 23.1 (2) and −85.6 (5)°, respectively. In the crystal, offset π-stacking interactions between the dihydroquinoxaline moieties form oblique stacks, which are connected into layers parallel to the bc plane by C—H⋯O hydrogen bonds and C—H⋯π(ring) interactions. Additional C—H⋯π(ring) interactions tie the layers together. The model was refined as a two-component twin.
of the title compound, CKeywords: crystal structure; oxirane; quinoxalone; hydrogen bond; π-stacking.
CCDC reference: 1838727
Structure description
In a continuation of our previous work on the synthesis and biological properties of quinoxaline derivatives (Ramli & Essassi, 2015; Abad et al., 2018), we report herein on the preparation and of the title compound.
The ) consists of two independent molecules differing in the orientation of the pendant phenyl and oxirane substituents. Thus the N1—C7—C9—C10 torsion angle is 27.8 (7)° while the N3—C24—C26—C27 angle is −22.8 (7)°. In addition, the C1—N2—C15—C16 torsion angle is −93.7 (5)° while the C18—N4—C32—C33 angle is 94.1 (5)°. The dihydroquinoxalone moieties are virtually planar (r.m.s. deviations for the C1 and C18 molecules = 0.026 and 0.024 Å, respectively) with the largest deviation from the mean plane being the carbonyl carbon atoms C8 [0.038 (5) Å] and C25 [0.038 (5) Å]. The oxygen atoms O1 and O3 were not included in the mean-plane calculations and lie, respectively, 0.098 (4) and 0.109 (4) Å from the mean planes.
(Fig. 1In the crystal, the two independent molecules form oblique stacks along the b-axis direction in an alternating head-to-tail fashion through offset π-stacking interactions between the dihydroquinoxalone moieties [centroid–centroid separations = 3.703 (3) and 3.546 (3) Å for the C1/C6/N1/C7/C8/N2 ring and the C18–C25 rings at (−x + 1, y − , −z + 1) and at (−x + 1, y + , −z + 1), respectively, and 3.620 (3) and 3.616 (3) Å for the C1–C6 ring and the C18/C23/N3/C24/C25/N4 rings at (−x + 1, y − , −z + 1) and (−x + 1, y + , −z + 1), respectively]. These interactions are accompanied by C—H⋯O hydrogen bonds as well as C17—H17A⋯Cg4 and C34—H34B⋯Cg9 C—H⋯π interactions (Table 1), which reinforce and connect the stacks, forming layers parallel to the bc plane (Fig. 2). The layers are weakly connected along the a-axis direction by complementary C28—H28⋯Cg9 interactions (Table 1 and Fig. 3).
Synthesis and crystallization
To a solution of 2-oxo-3-phenyl-1,2-dihydroquinoxaline (0.5 g, 2.25 mmol) in dichloromethane (20 ml) were added 2-(chloromethyl)oxirane (0.2 ml, 2.25 mmol), sodium hydroxide (0.1 g, 2.25 mmol) and a catalytic quantity of tetra-n-butylammonium bromide. The reaction mixture was stirred at room temperature for 24 h. The solution was filtered and the solvent removed under reduced pressure. The residue thus obtained was chromatographed on a silica gel column using a hexane/ethyl acetate 9:1 mixture as The solid obtained was recrystallized from ethanol solution to afford colourless plates of the title compound.
Refinement
Crystal data, data collection and structure . The model was refined as a two-component twin.
details are summarized in Table 2
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Structural data
CCDC reference: 1838727
https://doi.org/10.1107/S2414314618006107/hb4230sup1.cif
contains datablocks global, I. DOI:Structure factors: contains datablock I. DOI: https://doi.org/10.1107/S2414314618006107/hb4230Isup2.hkl
Supporting information file. DOI: https://doi.org/10.1107/S2414314618006107/hb4230Isup3.cdx
Supporting information file. DOI: https://doi.org/10.1107/S2414314618006107/hb4230Isup4.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: SHELXL2018 (Sheldrick, 2015b); molecular graphics: DIAMOND (Brandenburg & Putz, 2012); software used to prepare material for publication: SHELXTL (Sheldrick, 2008).C17H14N2O2 | F(000) = 584 |
Mr = 278.30 | Dx = 1.343 Mg m−3 |
Monoclinic, P21 | Cu Kα radiation, λ = 1.54178 Å |
a = 12.7853 (3) Å | Cell parameters from 9964 reflections |
b = 7.0167 (2) Å | θ = 3.5–72.5° |
c = 15.4215 (4) Å | µ = 0.72 mm−1 |
β = 95.718 (1)° | T = 200 K |
V = 1376.59 (6) Å3 | Plate, colourless |
Z = 4 | 0.32 × 0.09 × 0.02 mm |
Bruker D8 VENTURE PHOTON 100 CMOS diffractometer | 17578 independent reflections |
Radiation source: INCOATEC IµS micro-focus source | 13057 reflections with I > 2σ(I) |
Mirror monochromator | Rint = 0.053 |
Detector resolution: 10.4167 pixels mm-1 | θmax = 72.5°, θmin = 2.9° |
ω scans | h = −15→15 |
Absorption correction: multi-scan (TWINABS; Sheldrick, 2009) | k = −8→8 |
Tmin = 0.80, Tmax = 0.99 | l = −16→17 |
17578 measured reflections |
Refinement on F2 | Hydrogen site location: inferred from neighbouring sites |
Least-squares matrix: full | H-atom parameters constrained |
R[F2 > 2σ(F2)] = 0.062 | w = 1/[σ2(Fo2) + (0.0548P)2 + 0.1212P] where P = (Fo2 + 2Fc2)/3 |
wR(F2) = 0.147 | (Δ/σ)max < 0.001 |
S = 1.04 | Δρmax = 0.20 e Å−3 |
17578 reflections | Δρmin = −0.19 e Å−3 |
381 parameters | Extinction correction: SHELXL2018 (Sheldrick, 2015b), Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4 |
1 restraint | Extinction coefficient: 0.0029 (8) |
Primary atom site location: structure-invariant direct methods | Absolute structure: Flack x determined using 1479 quotients [(I+)-(I-)]/[(I+)+(I-)] (Parsons et al., 2013) |
Secondary atom site location: difference Fourier map | Absolute structure parameter: 0.32 (17) |
Experimental. Analysis of 995 reflections having I/σ(I) > 12 and chosen from the full data set withCELL_NOW (Sheldrick, 2008) showed the crystal to belong to the monoclinic system and to be twinned by a 180° rotation about the c axis. The raw data were processed using the multi-component version of SAINT under control of the two-component orientation file generated by CELL_NOW. |
Geometry. All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. |
Refinement. Refinement of F2 against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F2, conventional R-factors R are based on F, with F set to zero for negative F2. The threshold expression of F2 > 2sigma(F2) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F2 are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. H-atoms attached to carbon were placed in calculated positions (C—H = 0.95 - 1.00 Å) and included as riding contributions with isotropic displacement parameters 1.2 - 1.5 times those of the attached atoms. Refined as a 2-component twin. |
x | y | z | Uiso*/Ueq | ||
O1 | 0.4028 (3) | 0.3996 (6) | 0.4830 (2) | 0.0412 (10) | |
O2 | 0.6415 (3) | 0.5409 (6) | 0.7106 (2) | 0.0431 (10) | |
N1 | 0.2018 (3) | 0.4840 (6) | 0.6230 (3) | 0.0312 (10) | |
N2 | 0.4120 (3) | 0.3738 (6) | 0.6307 (3) | 0.0274 (9) | |
C1 | 0.3661 (4) | 0.3984 (7) | 0.7081 (3) | 0.0273 (11) | |
C2 | 0.4211 (4) | 0.3726 (7) | 0.7906 (3) | 0.0330 (12) | |
H2 | 0.493027 | 0.336082 | 0.795627 | 0.040* | |
C3 | 0.3705 (4) | 0.4005 (8) | 0.8644 (4) | 0.0367 (13) | |
H3 | 0.408232 | 0.383106 | 0.920066 | 0.044* | |
C4 | 0.2656 (4) | 0.4535 (8) | 0.8589 (3) | 0.0376 (12) | |
H4 | 0.231870 | 0.471955 | 0.910437 | 0.045* | |
C5 | 0.2108 (4) | 0.4791 (7) | 0.7786 (3) | 0.0355 (12) | |
H5 | 0.138839 | 0.515034 | 0.774595 | 0.043* | |
C6 | 0.2607 (4) | 0.4525 (7) | 0.7020 (3) | 0.0280 (10) | |
C7 | 0.2469 (4) | 0.4674 (7) | 0.5511 (3) | 0.0300 (11) | |
C8 | 0.3583 (4) | 0.4127 (7) | 0.5506 (3) | 0.0302 (11) | |
C9 | 0.1817 (4) | 0.5144 (7) | 0.4689 (3) | 0.0330 (12) | |
C10 | 0.1001 (4) | 0.6458 (8) | 0.4718 (4) | 0.0404 (13) | |
H10 | 0.087995 | 0.701449 | 0.526022 | 0.049* | |
C11 | 0.0361 (5) | 0.6973 (10) | 0.3972 (4) | 0.0535 (17) | |
H11 | −0.017817 | 0.789438 | 0.400177 | 0.064* | |
C12 | 0.0522 (5) | 0.6125 (11) | 0.3188 (4) | 0.0587 (19) | |
H12 | 0.008554 | 0.645194 | 0.267447 | 0.070* | |
C13 | 0.1312 (5) | 0.4809 (11) | 0.3151 (4) | 0.0556 (18) | |
H13 | 0.140663 | 0.421709 | 0.260983 | 0.067* | |
C14 | 0.1974 (4) | 0.4325 (9) | 0.3886 (4) | 0.0438 (14) | |
H14 | 0.253044 | 0.344351 | 0.384318 | 0.053* | |
C15 | 0.5214 (4) | 0.3070 (7) | 0.6294 (4) | 0.0314 (11) | |
H15A | 0.525781 | 0.225748 | 0.577398 | 0.038* | |
H15B | 0.540449 | 0.227476 | 0.681603 | 0.038* | |
C16 | 0.5989 (4) | 0.4659 (7) | 0.6277 (3) | 0.0317 (11) | |
H16 | 0.586626 | 0.559289 | 0.578804 | 0.038* | |
C17 | 0.7079 (4) | 0.4289 (9) | 0.6599 (4) | 0.0438 (14) | |
H17A | 0.726594 | 0.298482 | 0.680493 | 0.053* | |
H17B | 0.763298 | 0.496150 | 0.631421 | 0.053* | |
O3 | 0.5845 (3) | 0.3974 (6) | −0.0013 (2) | 0.0383 (9) | |
O4 | 0.3526 (3) | 0.5469 (6) | 0.1877 (2) | 0.0439 (10) | |
N3 | 0.7867 (3) | 0.4763 (6) | 0.1718 (3) | 0.0286 (9) | |
N4 | 0.5762 (3) | 0.3701 (6) | 0.1442 (3) | 0.0262 (9) | |
C18 | 0.6218 (4) | 0.3933 (7) | 0.2297 (3) | 0.0239 (10) | |
C19 | 0.5665 (4) | 0.3672 (7) | 0.3026 (3) | 0.0310 (11) | |
H19 | 0.494428 | 0.331880 | 0.295367 | 0.037* | |
C20 | 0.6173 (4) | 0.3931 (7) | 0.3853 (3) | 0.0313 (11) | |
H20 | 0.579565 | 0.374620 | 0.434718 | 0.038* | |
C21 | 0.7226 (4) | 0.4457 (8) | 0.3972 (3) | 0.0362 (12) | |
H21 | 0.756429 | 0.463735 | 0.454327 | 0.043* | |
C22 | 0.7776 (4) | 0.4715 (7) | 0.3258 (3) | 0.0337 (12) | |
H22 | 0.849695 | 0.506572 | 0.333827 | 0.040* | |
C23 | 0.7282 (4) | 0.4465 (7) | 0.2412 (3) | 0.0273 (10) | |
C24 | 0.7419 (4) | 0.4606 (7) | 0.0924 (3) | 0.0275 (10) | |
C25 | 0.6298 (4) | 0.4082 (7) | 0.0731 (3) | 0.0274 (11) | |
C26 | 0.8073 (4) | 0.5017 (7) | 0.0204 (3) | 0.0295 (11) | |
C27 | 0.8958 (4) | 0.6170 (7) | 0.0383 (4) | 0.0367 (12) | |
H27 | 0.910857 | 0.669315 | 0.094984 | 0.044* | |
C28 | 0.9622 (5) | 0.6563 (9) | −0.0252 (4) | 0.0454 (14) | |
H28 | 1.022013 | 0.735342 | −0.012094 | 0.054* | |
C29 | 0.9411 (5) | 0.5801 (9) | −0.1077 (4) | 0.0473 (15) | |
H29 | 0.986184 | 0.607713 | −0.151485 | 0.057* | |
C30 | 0.8555 (4) | 0.4651 (10) | −0.1264 (4) | 0.0487 (15) | |
H30 | 0.842563 | 0.410186 | −0.182770 | 0.058* | |
C31 | 0.7869 (4) | 0.4276 (8) | −0.0634 (3) | 0.0378 (12) | |
H31 | 0.726240 | 0.351452 | −0.077786 | 0.045* | |
C32 | 0.4665 (4) | 0.3043 (7) | 0.1257 (3) | 0.0300 (11) | |
H32A | 0.447343 | 0.225915 | 0.175054 | 0.036* | |
H32B | 0.461079 | 0.222681 | 0.073054 | 0.036* | |
C33 | 0.3905 (4) | 0.4656 (7) | 0.1115 (3) | 0.0310 (11) | |
H33 | 0.402167 | 0.555837 | 0.063156 | 0.037* | |
C34 | 0.2818 (4) | 0.4357 (9) | 0.1292 (4) | 0.0464 (14) | |
H34A | 0.226085 | 0.504144 | 0.092328 | 0.056* | |
H34B | 0.261803 | 0.307448 | 0.148635 | 0.056* |
U11 | U22 | U33 | U12 | U13 | U23 | |
O1 | 0.036 (2) | 0.053 (3) | 0.036 (2) | 0.0029 (18) | 0.0109 (16) | −0.0019 (18) |
O2 | 0.041 (2) | 0.042 (2) | 0.046 (2) | −0.0012 (17) | 0.0010 (17) | −0.0139 (18) |
N1 | 0.028 (2) | 0.030 (2) | 0.036 (3) | −0.0024 (17) | 0.0041 (17) | 0.0001 (19) |
N2 | 0.025 (2) | 0.024 (2) | 0.033 (2) | 0.0000 (16) | 0.0021 (16) | 0.0001 (18) |
C1 | 0.032 (3) | 0.018 (2) | 0.033 (3) | −0.0050 (19) | 0.006 (2) | −0.001 (2) |
C2 | 0.033 (3) | 0.029 (3) | 0.036 (3) | −0.004 (2) | 0.001 (2) | 0.003 (2) |
C3 | 0.045 (3) | 0.030 (3) | 0.035 (3) | −0.008 (2) | 0.003 (2) | 0.002 (2) |
C4 | 0.045 (3) | 0.037 (3) | 0.033 (3) | −0.009 (3) | 0.012 (2) | −0.001 (2) |
C5 | 0.034 (3) | 0.032 (3) | 0.042 (3) | −0.003 (2) | 0.008 (2) | 0.000 (3) |
C6 | 0.029 (2) | 0.023 (2) | 0.032 (3) | −0.003 (2) | 0.0060 (19) | 0.000 (2) |
C7 | 0.029 (3) | 0.025 (3) | 0.036 (3) | −0.003 (2) | 0.000 (2) | −0.002 (2) |
C8 | 0.029 (3) | 0.024 (3) | 0.037 (3) | −0.003 (2) | 0.004 (2) | −0.003 (2) |
C9 | 0.032 (3) | 0.033 (3) | 0.033 (3) | −0.006 (2) | 0.000 (2) | 0.000 (2) |
C10 | 0.029 (3) | 0.044 (3) | 0.048 (3) | 0.001 (2) | −0.001 (2) | 0.001 (3) |
C11 | 0.031 (3) | 0.065 (4) | 0.062 (5) | 0.002 (3) | −0.004 (3) | 0.011 (3) |
C12 | 0.037 (4) | 0.091 (6) | 0.046 (4) | −0.014 (3) | −0.007 (3) | 0.013 (4) |
C13 | 0.046 (4) | 0.086 (5) | 0.035 (3) | −0.011 (3) | 0.000 (2) | −0.003 (3) |
C14 | 0.039 (3) | 0.054 (4) | 0.038 (3) | −0.003 (3) | 0.003 (2) | −0.006 (3) |
C15 | 0.028 (3) | 0.027 (3) | 0.039 (3) | 0.003 (2) | 0.003 (2) | 0.000 (2) |
C16 | 0.031 (3) | 0.033 (3) | 0.031 (3) | −0.001 (2) | 0.0029 (19) | −0.001 (2) |
C17 | 0.029 (3) | 0.045 (3) | 0.058 (4) | 0.002 (3) | 0.004 (2) | −0.011 (3) |
O3 | 0.034 (2) | 0.047 (2) | 0.033 (2) | −0.0020 (17) | −0.0005 (15) | 0.0004 (18) |
O4 | 0.044 (2) | 0.043 (2) | 0.046 (2) | 0.0040 (18) | 0.0080 (17) | −0.0128 (18) |
N3 | 0.027 (2) | 0.027 (2) | 0.031 (2) | −0.0012 (17) | 0.0046 (16) | 0.0000 (18) |
N4 | 0.023 (2) | 0.024 (2) | 0.032 (2) | −0.0003 (16) | 0.0036 (16) | 0.0003 (18) |
C18 | 0.028 (3) | 0.017 (2) | 0.026 (3) | 0.0034 (19) | 0.0027 (18) | 0.0013 (19) |
C19 | 0.029 (3) | 0.025 (3) | 0.039 (3) | 0.004 (2) | 0.007 (2) | 0.005 (2) |
C20 | 0.037 (3) | 0.029 (3) | 0.029 (3) | 0.005 (2) | 0.008 (2) | 0.003 (2) |
C21 | 0.044 (3) | 0.034 (3) | 0.031 (3) | 0.008 (3) | 0.004 (2) | 0.004 (2) |
C22 | 0.031 (3) | 0.031 (3) | 0.038 (3) | −0.001 (2) | 0.000 (2) | 0.000 (2) |
C23 | 0.032 (3) | 0.019 (2) | 0.031 (3) | 0.001 (2) | 0.005 (2) | 0.001 (2) |
C24 | 0.029 (3) | 0.022 (2) | 0.032 (3) | 0.000 (2) | 0.0036 (19) | 0.000 (2) |
C25 | 0.028 (2) | 0.022 (2) | 0.032 (3) | 0.0014 (19) | 0.004 (2) | 0.001 (2) |
C26 | 0.026 (3) | 0.027 (3) | 0.037 (3) | 0.005 (2) | 0.006 (2) | 0.000 (2) |
C27 | 0.038 (3) | 0.033 (3) | 0.041 (3) | −0.003 (2) | 0.013 (2) | −0.004 (2) |
C28 | 0.038 (3) | 0.043 (3) | 0.057 (4) | −0.005 (3) | 0.016 (3) | 0.001 (3) |
C29 | 0.044 (4) | 0.059 (4) | 0.042 (4) | 0.007 (3) | 0.019 (3) | 0.009 (3) |
C30 | 0.045 (3) | 0.067 (4) | 0.035 (3) | 0.010 (3) | 0.007 (2) | −0.001 (3) |
C31 | 0.037 (3) | 0.041 (3) | 0.035 (3) | 0.003 (3) | 0.004 (2) | −0.005 (2) |
C32 | 0.027 (3) | 0.028 (3) | 0.035 (3) | −0.003 (2) | 0.004 (2) | −0.002 (2) |
C33 | 0.029 (3) | 0.031 (3) | 0.033 (3) | 0.002 (2) | 0.0030 (19) | 0.000 (2) |
C34 | 0.031 (3) | 0.044 (3) | 0.064 (4) | −0.002 (3) | 0.004 (2) | −0.005 (3) |
O1—C8 | 1.239 (6) | O3—C25 | 1.235 (6) |
O2—C16 | 1.438 (6) | O4—C33 | 1.434 (6) |
O2—C17 | 1.443 (6) | O4—C34 | 1.442 (7) |
N1—C7 | 1.304 (6) | N3—C24 | 1.304 (6) |
N1—C6 | 1.385 (6) | N3—C23 | 1.381 (6) |
N2—C8 | 1.380 (6) | N4—C25 | 1.376 (6) |
N2—C1 | 1.393 (6) | N4—C18 | 1.397 (6) |
N2—C15 | 1.476 (6) | N4—C32 | 1.477 (6) |
C1—C6 | 1.394 (7) | C18—C19 | 1.398 (7) |
C1—C2 | 1.403 (7) | C18—C23 | 1.405 (6) |
C2—C3 | 1.377 (7) | C19—C20 | 1.385 (7) |
C2—H2 | 0.9500 | C19—H19 | 0.9500 |
C3—C4 | 1.386 (8) | C20—C21 | 1.391 (7) |
C3—H3 | 0.9500 | C20—H20 | 0.9500 |
C4—C5 | 1.373 (7) | C21—C22 | 1.377 (7) |
C4—H4 | 0.9500 | C21—H21 | 0.9500 |
C5—C6 | 1.410 (7) | C22—C23 | 1.402 (7) |
C5—H5 | 0.9500 | C22—H22 | 0.9500 |
C7—C8 | 1.476 (7) | C24—C25 | 1.481 (6) |
C7—C9 | 1.484 (7) | C24—C26 | 1.484 (7) |
C9—C10 | 1.397 (7) | C26—C31 | 1.393 (7) |
C9—C14 | 1.397 (7) | C26—C27 | 1.397 (7) |
C10—C11 | 1.391 (8) | C27—C28 | 1.386 (8) |
C10—H10 | 0.9500 | C27—H27 | 0.9500 |
C11—C12 | 1.381 (9) | C28—C29 | 1.381 (8) |
C11—H11 | 0.9500 | C28—H28 | 0.9500 |
C12—C13 | 1.374 (10) | C29—C30 | 1.368 (8) |
C12—H12 | 0.9500 | C29—H29 | 0.9500 |
C13—C14 | 1.388 (8) | C30—C31 | 1.397 (8) |
C13—H13 | 0.9500 | C30—H30 | 0.9500 |
C14—H14 | 0.9500 | C31—H31 | 0.9500 |
C15—C16 | 1.494 (7) | C32—C33 | 1.493 (7) |
C15—H15A | 0.9900 | C32—H32A | 0.9900 |
C15—H15B | 0.9900 | C32—H32B | 0.9900 |
C16—C17 | 1.455 (7) | C33—C34 | 1.459 (7) |
C16—H16 | 1.0000 | C33—H33 | 1.0000 |
C17—H17A | 0.9900 | C34—H34A | 0.9900 |
C17—H17B | 0.9900 | C34—H34B | 0.9900 |
C16—O2—C17 | 60.7 (3) | C33—O4—C34 | 61.0 (3) |
C7—N1—C6 | 119.1 (4) | C24—N3—C23 | 119.5 (4) |
C8—N2—C1 | 121.9 (4) | C25—N4—C18 | 122.3 (4) |
C8—N2—C15 | 116.0 (4) | C25—N4—C32 | 116.4 (4) |
C1—N2—C15 | 122.2 (4) | C18—N4—C32 | 121.2 (4) |
N2—C1—C6 | 117.6 (4) | N4—C18—C19 | 123.1 (4) |
N2—C1—C2 | 123.0 (5) | N4—C18—C23 | 117.2 (4) |
C6—C1—C2 | 119.4 (5) | C19—C18—C23 | 119.6 (4) |
C3—C2—C1 | 119.7 (5) | C20—C19—C18 | 119.7 (5) |
C3—C2—H2 | 120.1 | C20—C19—H19 | 120.2 |
C1—C2—H2 | 120.1 | C18—C19—H19 | 120.2 |
C2—C3—C4 | 121.3 (5) | C19—C20—C21 | 121.0 (5) |
C2—C3—H3 | 119.4 | C19—C20—H20 | 119.5 |
C4—C3—H3 | 119.4 | C21—C20—H20 | 119.5 |
C5—C4—C3 | 119.6 (5) | C22—C21—C20 | 119.6 (5) |
C5—C4—H4 | 120.2 | C22—C21—H21 | 120.2 |
C3—C4—H4 | 120.2 | C20—C21—H21 | 120.2 |
C4—C5—C6 | 120.4 (5) | C21—C22—C23 | 120.6 (5) |
C4—C5—H5 | 119.8 | C21—C22—H22 | 119.7 |
C6—C5—H5 | 119.8 | C23—C22—H22 | 119.7 |
N1—C6—C1 | 122.7 (4) | N3—C23—C22 | 118.2 (4) |
N1—C6—C5 | 117.7 (5) | N3—C23—C18 | 122.4 (4) |
C1—C6—C5 | 119.7 (5) | C22—C23—C18 | 119.4 (4) |
N1—C7—C8 | 122.4 (4) | N3—C24—C25 | 122.4 (4) |
N1—C7—C9 | 116.7 (4) | N3—C24—C26 | 117.3 (4) |
C8—C7—C9 | 120.9 (5) | C25—C24—C26 | 120.3 (4) |
O1—C8—N2 | 120.6 (4) | O3—C25—N4 | 120.2 (4) |
O1—C8—C7 | 123.2 (5) | O3—C25—C24 | 123.9 (4) |
N2—C8—C7 | 116.2 (4) | N4—C25—C24 | 115.9 (4) |
C10—C9—C14 | 118.2 (5) | C31—C26—C27 | 118.2 (5) |
C10—C9—C7 | 118.5 (5) | C31—C26—C24 | 123.7 (5) |
C14—C9—C7 | 123.3 (5) | C27—C26—C24 | 118.0 (5) |
C11—C10—C9 | 121.7 (6) | C28—C27—C26 | 121.1 (5) |
C11—C10—H10 | 119.2 | C28—C27—H27 | 119.5 |
C9—C10—H10 | 119.2 | C26—C27—H27 | 119.5 |
C12—C11—C10 | 119.1 (6) | C29—C28—C27 | 119.8 (6) |
C12—C11—H11 | 120.5 | C29—C28—H28 | 120.1 |
C10—C11—H11 | 120.5 | C27—C28—H28 | 120.1 |
C13—C12—C11 | 120.0 (6) | C30—C29—C28 | 120.1 (5) |
C13—C12—H12 | 120.0 | C30—C29—H29 | 120.0 |
C11—C12—H12 | 120.0 | C28—C29—H29 | 120.0 |
C12—C13—C14 | 121.4 (6) | C29—C30—C31 | 120.6 (5) |
C12—C13—H13 | 119.3 | C29—C30—H30 | 119.7 |
C14—C13—H13 | 119.3 | C31—C30—H30 | 119.7 |
C13—C14—C9 | 119.6 (6) | C26—C31—C30 | 120.2 (5) |
C13—C14—H14 | 120.2 | C26—C31—H31 | 119.9 |
C9—C14—H14 | 120.2 | C30—C31—H31 | 119.9 |
N2—C15—C16 | 113.2 (4) | N4—C32—C33 | 112.5 (4) |
N2—C15—H15A | 108.9 | N4—C32—H32A | 109.1 |
C16—C15—H15A | 108.9 | C33—C32—H32A | 109.1 |
N2—C15—H15B | 108.9 | N4—C32—H32B | 109.1 |
C16—C15—H15B | 108.9 | C33—C32—H32B | 109.1 |
H15A—C15—H15B | 107.7 | H32A—C32—H32B | 107.8 |
O2—C16—C17 | 59.8 (3) | O4—C33—C34 | 59.8 (3) |
O2—C16—C15 | 116.8 (4) | O4—C33—C32 | 116.7 (4) |
C17—C16—C15 | 118.4 (5) | C34—C33—C32 | 118.8 (5) |
O2—C16—H16 | 116.6 | O4—C33—H33 | 116.5 |
C17—C16—H16 | 116.6 | C34—C33—H33 | 116.5 |
C15—C16—H16 | 116.6 | C32—C33—H33 | 116.5 |
O2—C17—C16 | 59.5 (3) | O4—C34—C33 | 59.2 (3) |
O2—C17—H17A | 117.8 | O4—C34—H34A | 117.8 |
C16—C17—H17A | 117.8 | C33—C34—H34A | 117.8 |
O2—C17—H17B | 117.8 | O4—C34—H34B | 117.8 |
C16—C17—H17B | 117.8 | C33—C34—H34B | 117.8 |
H17A—C17—H17B | 115.0 | H34A—C34—H34B | 115.0 |
C8—N2—C1—C6 | 4.0 (7) | C25—N4—C18—C19 | 175.7 (4) |
C15—N2—C1—C6 | −176.7 (4) | C32—N4—C18—C19 | −3.8 (7) |
C8—N2—C1—C2 | −175.4 (4) | C25—N4—C18—C23 | −3.8 (7) |
C15—N2—C1—C2 | 3.8 (7) | C32—N4—C18—C23 | 176.7 (4) |
N2—C1—C2—C3 | 179.6 (4) | N4—C18—C19—C20 | −179.9 (4) |
C6—C1—C2—C3 | 0.2 (7) | C23—C18—C19—C20 | −0.3 (7) |
C1—C2—C3—C4 | 0.1 (8) | C18—C19—C20—C21 | 0.3 (8) |
C2—C3—C4—C5 | −0.1 (8) | C19—C20—C21—C22 | −0.4 (8) |
C3—C4—C5—C6 | −0.2 (8) | C20—C21—C22—C23 | 0.4 (8) |
C7—N1—C6—C1 | −1.8 (7) | C24—N3—C23—C22 | −177.6 (4) |
C7—N1—C6—C5 | 177.4 (4) | C24—N3—C23—C18 | 2.1 (7) |
N2—C1—C6—N1 | −0.7 (7) | C21—C22—C23—N3 | 179.3 (5) |
C2—C1—C6—N1 | 178.8 (5) | C21—C22—C23—C18 | −0.5 (8) |
N2—C1—C6—C5 | −180.0 (4) | N4—C18—C23—N3 | 0.3 (7) |
C2—C1—C6—C5 | −0.5 (7) | C19—C18—C23—N3 | −179.3 (4) |
C4—C5—C6—N1 | −178.8 (4) | N4—C18—C23—C22 | −180.0 (4) |
C4—C5—C6—C1 | 0.5 (8) | C19—C18—C23—C22 | 0.4 (7) |
C6—N1—C7—C8 | 1.2 (7) | C23—N3—C24—C25 | −1.1 (7) |
C6—N1—C7—C9 | −176.4 (4) | C23—N3—C24—C26 | 177.6 (4) |
C1—N2—C8—O1 | 176.1 (4) | C18—N4—C25—O3 | −175.4 (4) |
C15—N2—C8—O1 | −3.2 (7) | C32—N4—C25—O3 | 4.1 (7) |
C1—N2—C8—C7 | −4.6 (7) | C18—N4—C25—C24 | 4.7 (7) |
C15—N2—C8—C7 | 176.2 (4) | C32—N4—C25—C24 | −175.8 (4) |
N1—C7—C8—O1 | −178.7 (5) | N3—C24—C25—O3 | 177.9 (5) |
C9—C7—C8—O1 | −1.3 (8) | C26—C24—C25—O3 | −0.8 (7) |
N1—C7—C8—N2 | 1.9 (7) | N3—C24—C25—N4 | −2.2 (7) |
C9—C7—C8—N2 | 179.4 (4) | C26—C24—C25—N4 | 179.1 (4) |
N1—C7—C9—C10 | 27.8 (7) | N3—C24—C26—C31 | 155.4 (5) |
C8—C7—C9—C10 | −149.8 (5) | C25—C24—C26—C31 | −25.9 (7) |
N1—C7—C9—C14 | −151.7 (5) | N3—C24—C26—C27 | −22.8 (7) |
C8—C7—C9—C14 | 30.7 (8) | C25—C24—C26—C27 | 155.9 (5) |
C14—C9—C10—C11 | −0.8 (8) | C31—C26—C27—C28 | −0.3 (8) |
C7—C9—C10—C11 | 179.7 (5) | C24—C26—C27—C28 | 178.0 (5) |
C9—C10—C11—C12 | 1.7 (9) | C26—C27—C28—C29 | −0.2 (9) |
C10—C11—C12—C13 | −0.7 (10) | C27—C28—C29—C30 | −0.5 (9) |
C11—C12—C13—C14 | −1.2 (10) | C28—C29—C30—C31 | 1.8 (9) |
C12—C13—C14—C9 | 2.1 (10) | C27—C26—C31—C30 | 1.6 (8) |
C10—C9—C14—C13 | −1.1 (9) | C24—C26—C31—C30 | −176.6 (5) |
C7—C9—C14—C13 | 178.4 (6) | C29—C30—C31—C26 | −2.4 (9) |
C8—N2—C15—C16 | 85.6 (5) | C25—N4—C32—C33 | −85.4 (5) |
C1—N2—C15—C16 | −93.7 (5) | C18—N4—C32—C33 | 94.1 (5) |
C17—O2—C16—C15 | 108.8 (5) | C34—O4—C33—C32 | −109.3 (5) |
N2—C15—C16—O2 | 87.8 (5) | N4—C32—C33—O4 | −85.6 (5) |
N2—C15—C16—C17 | 156.3 (4) | N4—C32—C33—C34 | −154.1 (5) |
C15—C16—C17—O2 | −106.2 (5) | C32—C33—C34—O4 | 105.9 (5) |
Cg4 and Cg9 are the centroids of the C9–C14 and C26–C31 benzene rings, respectively. |
D—H···A | D—H | H···A | D···A | D—H···A |
C3—H3···O3i | 0.95 | 2.45 | 3.263 (7) | 143 |
C16—H16···O1ii | 1.00 | 2.58 | 3.489 (7) | 151 |
C20—H20···O1 | 0.95 | 2.46 | 3.258 (6) | 142 |
C32—H32A···O2iii | 0.99 | 2.55 | 3.520 (6) | 168 |
C32—H32B···O3iv | 0.99 | 2.58 | 3.465 (6) | 149 |
C33—H33···O3v | 1.00 | 2.59 | 3.504 (6) | 152 |
C17—H17A···Cg4iii | 0.99 | 2.91 | 3.556 (6) | 123 |
C28—H28···Cg9vi | 0.95 | 2.62 | 3.512 (2) | 156 |
C34—H34B···Cg9iv | 0.99 | 2.93 | 3.587 (6) | 125 |
Symmetry codes: (i) x, y, z+1; (ii) −x+1, y+1/2, −z+1; (iii) −x+1, y−1/2, −z+1; (iv) −x+1, y−1/2, −z; (v) −x+1, y+1/2, −z; (vi) −x+2, y+1/2, −z. |
Funding information
The support of NSF–MRI grant No. 1228232 for the purchase of the diffractometer and Tulane University for support of the Tulane Crystallography Laboratory are gratefully acknowledged.
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