organic compounds
1,4-Dibenzyl-6-chloroquinoxaline-2,3(1H,4H)-dione
aLaboratoire de Chimie Organique Appliquée, Faculté des Sciences et Techniques, Université Sidi Mohammed Ben Abdellah, Fès, Morocco, bDepartment of Chemistry, Keene State College, 229 Main Street, Keene, NH 03435-2001, USA, and cLaboratoire de Chimie Organique Hétérocyclique, Pôle de Compétences Pharmacochimie, Mohammed V University in Rabat, BP 1014, Avenue Ibn Batouta, Rabat, Morocco
*Correspondence e-mail: alieljanati@gmail.com
The title compound, C22H17ClN2O2, crystallizes with two independent molecules (A and B) in the The 6-chloroquinoxaline-2,3(1H,4H)-dione ring system is essentially planar. The dihedral angles between the mean planes of the 6-chloroquinoxaline-2,3(1H,4H)-dione ring and the phenyl rings of the benzyl substituents in the two molecules are 68.34 and 73.8 (7)° for A, and 73.8 (5) and 80.7 (1)° for B, so that these rings point away from the quinoxaline ring system. In the crystal, weak C—H⋯O hydrogen bonds and π–π stacking interactions link the molecules into a three-dimensional network.
Keywords: crystal structure; quinoxaline; alkylation.
CCDC reference: 1556425
Structure description
Quinoxaline derivatives find use as anticancer (Noolvi et al., 2011), antidiabetic (Bahekar et al., 2007), antifungal (Xu and Fan, 2011), antiviral (Caia et al., 2008) and anti-inflammatory agents (Yan et al., 2007). As part of our work in this area, the synthesis and structure of the title compound, 1,4-dibenzyl-6-chloroquinoxaline-2,3(1H,4H)-dione are reported here.
The title compound crystallizes with two independent molecules (A and B) in the (Fig. 1). The 6-chloroquinoxaline-2,3(1H,4H)-dione unit is essentially planar. The maximum r.m.s. deviation from the mean plane through the non-H atoms of ring A (N1A/C1A/C2A/N2A/C3A/C8A/C7A/C5A/C4A) is 0.053 (2) Å for N2A and for ring B (N1B/C1B/C2B/N2B/C3B/C8B/C7B/C5B/C4B) is 0.096 (2) Å for N2B. The dihedral angles between the mean plane of the 6-chloroquinoxaline-2,3(1H,4H)-dione ring and its pendant phenyl rings are 68.3 (4) and 73.8 (7)° in molecule A, and 73.8 (5) and 80.7 (1)° in molecule B. The phenyl rings of the benzyl substituents in both molecules are inclined similarly, pointing away from the 6-chloroquinoxaline-2,3(1H,4H)-dione ring system. In the crystal, the two unique molecules are linked by weak C7B—H7B⋯O2A and C18B—H18B⋯O1A interactions ( Table 1) within the (Fig. 1). Additional C—H⋯O hydrogen bonds, together with π–π stacking interactions [Cg2–Cg7ii = 3.6611 (14) Å; symmetry code: (ii) x, 1 + y, z; Cg2 and Cg7 are the centroids of the C3A–C8A and C3B–C8B rings, respectively], link the molecules into a three-dimensional network (Fig. 2).
Synthesis and crystallization
To a solution of 6-chloroquinoxaline-2,3(1H,4H)-dione (0.3 g, 1.53 mmol) was added a DMF (20 ml) solution of potassium carbonate (0.53 g, 3.84 mmol), tetra-n-butylammonium bromide (0.07 g, 0.23 mmol) and benzyl chloride (0.44 ml, 3.79 mmol). Stirring was continued at room temperature for 36 h. The mixture was filtered and the solvent removed under reduced pressure. The residue obtained was dissolved in dichloromethane. The remaining salts were extracted with distilled water and the resulting mixture was chromatographed on a silica-gel column (eluent: ethyl acetate–hexane 1:2 v/v) to give the product in 87% yield. The compound was recrystallized from mixed solvents of dichloromethane–hexane (1:1 v/v) to give yellow crystals.
Refinement
Crystal data, data collection and structure .
details are summarized in Table 2Structural data
CCDC reference: 1556425
https://doi.org/10.1107/S2414314617009014/sj4123sup1.cif
contains datablock I. DOI:Supporting information file. DOI: https://doi.org/10.1107/S2414314617009014/sj4123Isup2.cdx
Structure factors: contains datablock I. DOI: https://doi.org/10.1107/S2414314617009014/sj4123Isup3.hkl
Supporting information file. DOI: https://doi.org/10.1107/S2414314617009014/sj4123Isup4.cml
Data collection: CrysAlis PRO Rigaku Oxford Diffraction, 2015); cell
CrysAlis PRO (Rigaku Oxford Diffraction, 2015); data reduction: CrysAlis PRO (Rigaku Oxford Diffraction, 2015); program(s) used to solve structure: SHELXT (Sheldrick, 2015a); program(s) used to refine structure: SHELXL2014 (Sheldrick, 2015b); molecular graphics: OLEX2 (Dolomanov et al., 2009); software used to prepare material for publication: OLEX2 (Dolomanov et al., 2009).C22H17ClN2O2 | F(000) = 3136 |
Mr = 376.82 | Dx = 1.358 Mg m−3 |
Monoclinic, I2/a | Cu Kα radiation, λ = 1.54184 Å |
a = 29.2234 (4) Å | Cell parameters from 6649 reflections |
b = 8.3076 (2) Å | θ = 4.6–71.4° |
c = 31.0407 (5) Å | µ = 1.99 mm−1 |
β = 101.859 (2)° | T = 293 K |
V = 7375.1 (2) Å3 | Prism, orange |
Z = 16 | 0.28 × 0.24 × 0.12 mm |
Rigaku Oxford Diffraction diffractometer | 6996 independent reflections |
Radiation source: fine-focus sealed X-ray tube, Enhance (Cu) X-ray Source | 5661 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.022 |
Detector resolution: 16.0416 pixels mm-1 | θmax = 71.3°, θmin = 3.8° |
ω scans | h = −35→25 |
Absorption correction: multi-scan (CrysAlis PRO; Rigaku Oxford Diffraction, 2015) | k = −10→9 |
Tmin = 0.500, Tmax = 1.000 | l = −37→38 |
14412 measured reflections |
Refinement on F2 | Primary atom site location: dual |
Least-squares matrix: full | Hydrogen site location: inferred from neighbouring sites |
R[F2 > 2σ(F2)] = 0.053 | H-atom parameters constrained |
wR(F2) = 0.156 | w = 1/[σ2(Fo2) + (0.0814P)2 + 5.5513P] where P = (Fo2 + 2Fc2)/3 |
S = 1.04 | (Δ/σ)max = 0.001 |
6996 reflections | Δρmax = 0.73 e Å−3 |
487 parameters | Δρmin = −0.37 e Å−3 |
0 restraints |
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. |
x | y | z | Uiso*/Ueq | ||
Cl1A | 0.62007 (2) | 0.06298 (9) | 0.71293 (2) | 0.0677 (2) | |
O1A | 0.53226 (7) | 0.1255 (3) | 0.47249 (6) | 0.0740 (6) | |
O2A | 0.46801 (6) | 0.3455 (3) | 0.48365 (6) | 0.0655 (5) | |
N1A | 0.55925 (6) | 0.1082 (2) | 0.54650 (6) | 0.0477 (4) | |
N2A | 0.48818 (6) | 0.3198 (2) | 0.55775 (6) | 0.0454 (4) | |
C1A | 0.53004 (8) | 0.1662 (3) | 0.50969 (7) | 0.0524 (6) | |
C2A | 0.49289 (8) | 0.2857 (3) | 0.51596 (7) | 0.0503 (5) | |
C3A | 0.51820 (7) | 0.2548 (2) | 0.59492 (7) | 0.0408 (4) | |
C4A | 0.55440 (7) | 0.1519 (3) | 0.58911 (7) | 0.0423 (4) | |
C5A | 0.58551 (7) | 0.0938 (3) | 0.62590 (7) | 0.0470 (5) | |
H5A | 0.6100 | 0.0268 | 0.6224 | 0.056* | |
C6A | 0.57996 (8) | 0.1356 (3) | 0.66737 (7) | 0.0481 (5) | |
C7A | 0.54401 (8) | 0.2333 (3) | 0.67408 (7) | 0.0472 (5) | |
H7A | 0.5406 | 0.2594 | 0.7024 | 0.057* | |
C8A | 0.51320 (7) | 0.2914 (3) | 0.63765 (7) | 0.0451 (5) | |
H8A | 0.4885 | 0.3565 | 0.6416 | 0.054* | |
C9A | 0.59406 (9) | −0.0137 (3) | 0.54046 (9) | 0.0590 (6) | |
H9AA | 0.5853 | −0.0581 | 0.5110 | 0.071* | |
H9AB | 0.5937 | −0.1007 | 0.5612 | 0.071* | |
C10A | 0.64278 (9) | 0.0527 (3) | 0.54688 (8) | 0.0578 (6) | |
C11A | 0.67930 (11) | −0.0200 (5) | 0.57570 (11) | 0.0882 (10) | |
H11A | 0.6738 | −0.1102 | 0.5917 | 0.106* | |
C12A | 0.72458 (12) | 0.0428 (8) | 0.58075 (13) | 0.1190 (18) | |
H12A | 0.7491 | −0.0036 | 0.6008 | 0.143* | |
C13A | 0.73264 (11) | 0.1720 (7) | 0.55627 (13) | 0.1114 (16) | |
H13A | 0.7628 | 0.2120 | 0.5592 | 0.134* | |
C14A | 0.69682 (11) | 0.2430 (5) | 0.52749 (12) | 0.0878 (10) | |
H14A | 0.7026 | 0.3315 | 0.5110 | 0.105* | |
C15A | 0.65210 (9) | 0.1837 (4) | 0.52278 (9) | 0.0649 (7) | |
H15A | 0.6278 | 0.2326 | 0.5031 | 0.078* | |
C16A | 0.45048 (8) | 0.4351 (3) | 0.56138 (8) | 0.0524 (5) | |
H16A | 0.4502 | 0.5208 | 0.5401 | 0.063* | |
H16B | 0.4572 | 0.4830 | 0.5905 | 0.063* | |
C17A | 0.40279 (8) | 0.3578 (3) | 0.55367 (8) | 0.0496 (5) | |
C18A | 0.37076 (10) | 0.3851 (4) | 0.51459 (9) | 0.0653 (7) | |
H18A | 0.3790 | 0.4489 | 0.4928 | 0.078* | |
C19A | 0.32639 (10) | 0.3172 (5) | 0.50810 (11) | 0.0825 (9) | |
H19A | 0.3051 | 0.3363 | 0.4819 | 0.099* | |
C20A | 0.31370 (10) | 0.2231 (4) | 0.53952 (13) | 0.0851 (10) | |
H20A | 0.2840 | 0.1773 | 0.5347 | 0.102* | |
C21A | 0.34496 (11) | 0.1960 (4) | 0.57839 (13) | 0.0856 (10) | |
H21A | 0.3363 | 0.1335 | 0.6002 | 0.103* | |
C22A | 0.38924 (9) | 0.2617 (4) | 0.58501 (10) | 0.0679 (7) | |
H22A | 0.4104 | 0.2407 | 0.6112 | 0.081* | |
Cl1B | 0.33081 (3) | 0.58144 (10) | 0.37621 (3) | 0.0797 (2) | |
O1B | 0.43598 (6) | 0.2708 (2) | 0.19629 (5) | 0.0610 (5) | |
O2B | 0.49943 (6) | 0.0979 (2) | 0.25341 (6) | 0.0627 (4) | |
N1B | 0.40704 (6) | 0.3788 (2) | 0.25221 (5) | 0.0427 (4) | |
N2B | 0.47554 (6) | 0.2118 (2) | 0.31145 (6) | 0.0429 (4) | |
C1B | 0.43687 (7) | 0.2823 (3) | 0.23545 (7) | 0.0445 (5) | |
C2B | 0.47303 (7) | 0.1879 (3) | 0.26761 (7) | 0.0457 (5) | |
C3B | 0.44279 (7) | 0.3067 (2) | 0.32762 (6) | 0.0405 (4) | |
C4B | 0.40761 (7) | 0.3855 (3) | 0.29761 (6) | 0.0401 (4) | |
C5B | 0.37306 (7) | 0.4698 (3) | 0.31310 (7) | 0.0468 (5) | |
H5B | 0.3489 | 0.5198 | 0.2935 | 0.056* | |
C6B | 0.37493 (9) | 0.4785 (3) | 0.35796 (8) | 0.0534 (6) | |
C7B | 0.41028 (9) | 0.4089 (3) | 0.38768 (7) | 0.0537 (6) | |
H7B | 0.4115 | 0.4190 | 0.4177 | 0.064* | |
C8B | 0.44431 (8) | 0.3231 (3) | 0.37248 (7) | 0.0484 (5) | |
H8B | 0.4686 | 0.2756 | 0.3926 | 0.058* | |
C9B | 0.37628 (8) | 0.4870 (3) | 0.22173 (7) | 0.0530 (5) | |
H9BA | 0.3877 | 0.4937 | 0.1946 | 0.064* | |
H9BB | 0.3782 | 0.5939 | 0.2345 | 0.064* | |
C10B | 0.32551 (8) | 0.4356 (3) | 0.21095 (7) | 0.0543 (6) | |
C11B | 0.31232 (10) | 0.2785 (4) | 0.20404 (11) | 0.0754 (8) | |
H11B | 0.3351 | 0.1991 | 0.2062 | 0.091* | |
C12B | 0.26533 (12) | 0.2348 (5) | 0.19378 (12) | 0.0946 (11) | |
H12B | 0.2570 | 0.1271 | 0.1893 | 0.113* | |
C13B | 0.23174 (11) | 0.3487 (7) | 0.19036 (12) | 0.1002 (13) | |
H13B | 0.2003 | 0.3196 | 0.1837 | 0.120* | |
C14B | 0.24408 (12) | 0.5056 (7) | 0.19666 (14) | 0.1053 (13) | |
H14B | 0.2210 | 0.5842 | 0.1939 | 0.126* | |
C15B | 0.29074 (11) | 0.5500 (5) | 0.20722 (12) | 0.0840 (9) | |
H15B | 0.2987 | 0.6580 | 0.2118 | 0.101* | |
C16B | 0.51314 (7) | 0.1264 (3) | 0.34172 (8) | 0.0487 (5) | |
H16C | 0.5194 | 0.0257 | 0.3282 | 0.058* | |
H16D | 0.5024 | 0.1007 | 0.3685 | 0.058* | |
C17B | 0.55802 (7) | 0.2199 (3) | 0.35376 (7) | 0.0421 (4) | |
C18B | 0.59036 (9) | 0.1716 (4) | 0.39071 (8) | 0.0608 (6) | |
H18B | 0.5827 | 0.0906 | 0.4086 | 0.073* | |
C19B | 0.63370 (9) | 0.2428 (4) | 0.40097 (10) | 0.0765 (9) | |
H19B | 0.6553 | 0.2084 | 0.4256 | 0.092* | |
C20B | 0.64540 (10) | 0.3633 (4) | 0.37538 (11) | 0.0771 (8) | |
H20B | 0.6750 | 0.4098 | 0.3822 | 0.093* | |
C21B | 0.61317 (10) | 0.4150 (4) | 0.33963 (11) | 0.0752 (8) | |
H21B | 0.6208 | 0.4987 | 0.3225 | 0.090* | |
C22B | 0.56949 (9) | 0.3443 (3) | 0.32867 (9) | 0.0597 (6) | |
H22B | 0.5479 | 0.3808 | 0.3043 | 0.072* |
U11 | U22 | U33 | U12 | U13 | U23 | |
Cl1A | 0.0533 (3) | 0.0909 (5) | 0.0550 (3) | −0.0014 (3) | 0.0025 (2) | 0.0022 (3) |
O1A | 0.0727 (12) | 0.1090 (16) | 0.0461 (9) | −0.0143 (11) | 0.0256 (8) | −0.0145 (10) |
O2A | 0.0555 (10) | 0.0907 (13) | 0.0486 (9) | −0.0118 (9) | 0.0072 (7) | 0.0121 (9) |
N1A | 0.0455 (10) | 0.0541 (11) | 0.0483 (10) | −0.0116 (8) | 0.0207 (8) | −0.0102 (8) |
N2A | 0.0446 (9) | 0.0484 (10) | 0.0447 (9) | −0.0100 (8) | 0.0126 (7) | 0.0000 (7) |
C1A | 0.0488 (12) | 0.0684 (15) | 0.0434 (11) | −0.0221 (11) | 0.0171 (9) | −0.0073 (10) |
C2A | 0.0458 (11) | 0.0622 (14) | 0.0445 (11) | −0.0206 (10) | 0.0131 (9) | 0.0012 (10) |
C3A | 0.0384 (10) | 0.0422 (10) | 0.0437 (10) | −0.0133 (8) | 0.0131 (8) | −0.0026 (8) |
C4A | 0.0417 (10) | 0.0447 (11) | 0.0438 (10) | −0.0138 (9) | 0.0162 (8) | −0.0058 (8) |
C5A | 0.0407 (11) | 0.0494 (12) | 0.0545 (12) | −0.0074 (9) | 0.0178 (9) | −0.0061 (9) |
C6A | 0.0423 (11) | 0.0549 (13) | 0.0471 (11) | −0.0126 (10) | 0.0095 (9) | −0.0019 (9) |
C7A | 0.0468 (11) | 0.0556 (13) | 0.0430 (10) | −0.0129 (10) | 0.0180 (9) | −0.0093 (9) |
C8A | 0.0415 (11) | 0.0485 (12) | 0.0488 (11) | −0.0077 (9) | 0.0173 (8) | −0.0051 (9) |
C9A | 0.0696 (16) | 0.0543 (14) | 0.0594 (13) | −0.0053 (12) | 0.0275 (12) | −0.0142 (11) |
C10A | 0.0566 (14) | 0.0690 (16) | 0.0523 (12) | 0.0075 (12) | 0.0218 (10) | −0.0145 (11) |
C11A | 0.0734 (19) | 0.125 (3) | 0.0725 (18) | 0.035 (2) | 0.0303 (15) | 0.0056 (19) |
C12A | 0.0602 (19) | 0.225 (6) | 0.074 (2) | 0.046 (3) | 0.0183 (16) | −0.006 (3) |
C13A | 0.0471 (17) | 0.205 (5) | 0.088 (2) | −0.002 (2) | 0.0270 (16) | −0.031 (3) |
C14A | 0.0553 (16) | 0.125 (3) | 0.092 (2) | −0.0153 (18) | 0.0360 (16) | −0.016 (2) |
C15A | 0.0499 (13) | 0.0809 (18) | 0.0682 (15) | −0.0032 (13) | 0.0221 (11) | −0.0108 (14) |
C16A | 0.0571 (13) | 0.0433 (12) | 0.0575 (13) | −0.0031 (10) | 0.0135 (10) | 0.0036 (10) |
C17A | 0.0471 (12) | 0.0470 (12) | 0.0550 (12) | 0.0051 (10) | 0.0111 (9) | 0.0001 (10) |
C18A | 0.0598 (15) | 0.0776 (18) | 0.0579 (14) | 0.0104 (13) | 0.0109 (11) | 0.0062 (13) |
C19A | 0.0545 (16) | 0.108 (3) | 0.0772 (19) | 0.0088 (17) | −0.0048 (14) | −0.0033 (18) |
C20A | 0.0480 (15) | 0.087 (2) | 0.115 (3) | −0.0072 (15) | 0.0055 (16) | 0.005 (2) |
C21A | 0.0598 (17) | 0.090 (2) | 0.107 (2) | −0.0122 (16) | 0.0174 (16) | 0.0273 (19) |
C22A | 0.0528 (14) | 0.0783 (18) | 0.0693 (16) | −0.0042 (13) | 0.0051 (12) | 0.0176 (14) |
Cl1B | 0.0706 (4) | 0.0975 (6) | 0.0804 (5) | 0.0044 (4) | 0.0372 (3) | −0.0286 (4) |
O1B | 0.0565 (9) | 0.0892 (13) | 0.0397 (8) | −0.0030 (9) | 0.0152 (7) | −0.0119 (8) |
O2B | 0.0569 (9) | 0.0730 (11) | 0.0633 (10) | 0.0107 (9) | 0.0242 (8) | −0.0098 (9) |
N1B | 0.0373 (8) | 0.0538 (10) | 0.0380 (8) | −0.0033 (8) | 0.0101 (6) | −0.0017 (7) |
N2B | 0.0373 (9) | 0.0470 (10) | 0.0455 (9) | −0.0039 (7) | 0.0114 (7) | −0.0022 (7) |
C1B | 0.0376 (10) | 0.0563 (12) | 0.0423 (10) | −0.0089 (9) | 0.0144 (8) | −0.0090 (9) |
C2B | 0.0400 (10) | 0.0522 (12) | 0.0480 (11) | −0.0046 (9) | 0.0163 (8) | −0.0062 (9) |
C3B | 0.0399 (10) | 0.0421 (10) | 0.0408 (10) | −0.0103 (8) | 0.0117 (8) | −0.0045 (8) |
C4B | 0.0376 (10) | 0.0446 (11) | 0.0404 (10) | −0.0103 (8) | 0.0133 (8) | −0.0070 (8) |
C5B | 0.0419 (11) | 0.0521 (12) | 0.0477 (11) | −0.0036 (10) | 0.0121 (9) | −0.0075 (9) |
C6B | 0.0568 (13) | 0.0551 (13) | 0.0544 (12) | −0.0127 (11) | 0.0259 (10) | −0.0167 (10) |
C7B | 0.0641 (14) | 0.0597 (14) | 0.0402 (11) | −0.0143 (11) | 0.0174 (10) | −0.0090 (10) |
C8B | 0.0537 (12) | 0.0506 (12) | 0.0413 (10) | −0.0104 (10) | 0.0104 (9) | −0.0014 (9) |
C9B | 0.0514 (12) | 0.0617 (14) | 0.0475 (11) | 0.0005 (11) | 0.0136 (9) | 0.0070 (10) |
C10B | 0.0468 (12) | 0.0740 (16) | 0.0419 (11) | 0.0031 (11) | 0.0084 (9) | 0.0051 (10) |
C11B | 0.0551 (15) | 0.081 (2) | 0.086 (2) | −0.0020 (14) | 0.0062 (14) | −0.0088 (16) |
C12B | 0.066 (2) | 0.114 (3) | 0.098 (2) | −0.027 (2) | 0.0026 (17) | −0.002 (2) |
C13B | 0.0479 (17) | 0.161 (4) | 0.087 (2) | −0.012 (2) | 0.0027 (14) | 0.019 (3) |
C14B | 0.0521 (18) | 0.145 (4) | 0.115 (3) | 0.027 (2) | 0.0084 (17) | 0.020 (3) |
C15B | 0.0609 (17) | 0.091 (2) | 0.096 (2) | 0.0137 (16) | 0.0063 (15) | 0.0105 (18) |
C16B | 0.0452 (11) | 0.0469 (12) | 0.0549 (12) | −0.0024 (9) | 0.0128 (9) | 0.0079 (10) |
C17B | 0.0408 (10) | 0.0445 (11) | 0.0427 (10) | 0.0037 (9) | 0.0124 (8) | −0.0012 (8) |
C18B | 0.0523 (13) | 0.0787 (17) | 0.0517 (12) | 0.0067 (12) | 0.0113 (10) | 0.0151 (12) |
C19B | 0.0472 (14) | 0.110 (2) | 0.0658 (16) | 0.0030 (15) | −0.0046 (12) | 0.0118 (16) |
C20B | 0.0448 (14) | 0.089 (2) | 0.092 (2) | −0.0110 (14) | 0.0015 (13) | −0.0024 (17) |
C21B | 0.0602 (16) | 0.0688 (18) | 0.094 (2) | −0.0184 (14) | 0.0098 (14) | 0.0180 (15) |
C22B | 0.0526 (13) | 0.0600 (14) | 0.0611 (14) | −0.0087 (11) | −0.0009 (10) | 0.0151 (12) |
Cl1A—C6A | 1.748 (2) | Cl1B—C6B | 1.737 (2) |
O1A—C1A | 1.218 (3) | O1B—C1B | 1.214 (3) |
O2A—C2A | 1.217 (3) | O2B—C2B | 1.220 (3) |
N1A—C1A | 1.366 (3) | N1B—C1B | 1.364 (3) |
N1A—C4A | 1.407 (3) | N1B—C4B | 1.407 (2) |
N1A—C9A | 1.474 (3) | N1B—C9B | 1.470 (3) |
N2A—C2A | 1.362 (3) | N2B—C2B | 1.362 (3) |
N2A—C3A | 1.406 (3) | N2B—C3B | 1.409 (3) |
N2A—C16A | 1.482 (3) | N2B—C16B | 1.472 (3) |
C1A—C2A | 1.513 (4) | C1B—C2B | 1.515 (3) |
C3A—C4A | 1.400 (3) | C3B—C4B | 1.400 (3) |
C3A—C8A | 1.398 (3) | C3B—C8B | 1.391 (3) |
C4A—C5A | 1.392 (3) | C4B—C5B | 1.393 (3) |
C5A—H5A | 0.9300 | C5B—H5B | 0.9300 |
C5A—C6A | 1.375 (3) | C5B—C6B | 1.384 (3) |
C6A—C7A | 1.377 (3) | C6B—C7B | 1.364 (4) |
C7A—H7A | 0.9300 | C7B—H7B | 0.9300 |
C7A—C8A | 1.380 (3) | C7B—C8B | 1.383 (3) |
C8A—H8A | 0.9300 | C8B—H8B | 0.9300 |
C9A—H9AA | 0.9700 | C9B—H9BA | 0.9700 |
C9A—H9AB | 0.9700 | C9B—H9BB | 0.9700 |
C9A—C10A | 1.502 (4) | C9B—C10B | 1.514 (3) |
C10A—C11A | 1.383 (4) | C10B—C11B | 1.365 (4) |
C10A—C15A | 1.379 (4) | C10B—C15B | 1.379 (4) |
C11A—H11A | 0.9300 | C11B—H11B | 0.9300 |
C11A—C12A | 1.401 (6) | C11B—C12B | 1.392 (4) |
C12A—H12A | 0.9300 | C12B—H12B | 0.9300 |
C12A—C13A | 1.363 (7) | C12B—C13B | 1.351 (6) |
C13A—H13A | 0.9300 | C13B—H13B | 0.9300 |
C13A—C14A | 1.363 (6) | C13B—C14B | 1.356 (6) |
C14A—H14A | 0.9300 | C14B—H14B | 0.9300 |
C14A—C15A | 1.376 (4) | C14B—C15B | 1.385 (5) |
C15A—H15A | 0.9300 | C15B—H15B | 0.9300 |
C16A—H16A | 0.9700 | C16B—H16C | 0.9700 |
C16A—H16B | 0.9700 | C16B—H16D | 0.9700 |
C16A—C17A | 1.508 (3) | C16B—C17B | 1.504 (3) |
C17A—C18A | 1.390 (3) | C17B—C18B | 1.387 (3) |
C17A—C22A | 1.378 (4) | C17B—C22B | 1.376 (3) |
C18A—H18A | 0.9300 | C18B—H18B | 0.9300 |
C18A—C19A | 1.390 (4) | C18B—C19B | 1.374 (4) |
C19A—H19A | 0.9300 | C19B—H19B | 0.9300 |
C19A—C20A | 1.359 (5) | C19B—C20B | 1.365 (5) |
C20A—H20A | 0.9300 | C20B—H20B | 0.9300 |
C20A—C21A | 1.374 (5) | C20B—C21B | 1.369 (4) |
C21A—H21A | 0.9300 | C21B—H21B | 0.9300 |
C21A—C22A | 1.380 (4) | C21B—C22B | 1.382 (4) |
C22A—H22A | 0.9300 | C22B—H22B | 0.9300 |
C1A—N1A—C4A | 121.9 (2) | C1B—N1B—C4B | 121.89 (18) |
C1A—N1A—C9A | 117.70 (19) | C1B—N1B—C9B | 117.92 (18) |
C4A—N1A—C9A | 120.2 (2) | C4B—N1B—C9B | 120.02 (18) |
C2A—N2A—C3A | 122.26 (19) | C2B—N2B—C3B | 122.42 (18) |
C2A—N2A—C16A | 115.41 (19) | C2B—N2B—C16B | 116.56 (18) |
C3A—N2A—C16A | 122.29 (18) | C3B—N2B—C16B | 120.96 (17) |
O1A—C1A—N1A | 123.3 (2) | O1B—C1B—N1B | 123.0 (2) |
O1A—C1A—C2A | 118.9 (2) | O1B—C1B—C2B | 119.2 (2) |
N1A—C1A—C2A | 117.75 (19) | N1B—C1B—C2B | 117.83 (18) |
O2A—C2A—N2A | 122.7 (2) | O2B—C2B—N2B | 122.8 (2) |
O2A—C2A—C1A | 119.0 (2) | O2B—C2B—C1B | 119.1 (2) |
N2A—C2A—C1A | 118.3 (2) | N2B—C2B—C1B | 118.04 (18) |
C4A—C3A—N2A | 119.30 (18) | C4B—C3B—N2B | 118.95 (18) |
C8A—C3A—N2A | 121.74 (19) | C8B—C3B—N2B | 121.8 (2) |
C8A—C3A—C4A | 118.96 (19) | C8B—C3B—C4B | 119.2 (2) |
C3A—C4A—N1A | 120.23 (19) | C3B—C4B—N1B | 120.27 (18) |
C5A—C4A—N1A | 120.5 (2) | C5B—C4B—N1B | 120.35 (19) |
C5A—C4A—C3A | 119.31 (19) | C5B—C4B—C3B | 119.38 (19) |
C4A—C5A—H5A | 120.1 | C4B—C5B—H5B | 120.3 |
C6A—C5A—C4A | 119.9 (2) | C6B—C5B—C4B | 119.5 (2) |
C6A—C5A—H5A | 120.1 | C6B—C5B—H5B | 120.3 |
C5A—C6A—Cl1A | 118.80 (18) | C5B—C6B—Cl1B | 118.4 (2) |
C5A—C6A—C7A | 122.1 (2) | C7B—C6B—Cl1B | 119.86 (18) |
C7A—C6A—Cl1A | 119.12 (17) | C7B—C6B—C5B | 121.7 (2) |
C6A—C7A—H7A | 120.9 | C6B—C7B—H7B | 120.5 |
C6A—C7A—C8A | 118.2 (2) | C6B—C7B—C8B | 119.0 (2) |
C8A—C7A—H7A | 120.9 | C8B—C7B—H7B | 120.5 |
C3A—C8A—H8A | 119.2 | C3B—C8B—H8B | 119.5 |
C7A—C8A—C3A | 121.6 (2) | C7B—C8B—C3B | 121.0 (2) |
C7A—C8A—H8A | 119.2 | C7B—C8B—H8B | 119.5 |
N1A—C9A—H9AA | 109.0 | N1B—C9B—H9BA | 108.7 |
N1A—C9A—H9AB | 109.0 | N1B—C9B—H9BB | 108.7 |
N1A—C9A—C10A | 113.0 (2) | N1B—C9B—C10B | 114.3 (2) |
H9AA—C9A—H9AB | 107.8 | H9BA—C9B—H9BB | 107.6 |
C10A—C9A—H9AA | 109.0 | C10B—C9B—H9BA | 108.7 |
C10A—C9A—H9AB | 109.0 | C10B—C9B—H9BB | 108.7 |
C11A—C10A—C9A | 120.7 (3) | C11B—C10B—C9B | 122.5 (2) |
C15A—C10A—C9A | 120.4 (2) | C11B—C10B—C15B | 117.8 (3) |
C15A—C10A—C11A | 118.9 (3) | C15B—C10B—C9B | 119.7 (3) |
C10A—C11A—H11A | 120.2 | C10B—C11B—H11B | 119.4 |
C10A—C11A—C12A | 119.7 (4) | C10B—C11B—C12B | 121.2 (3) |
C12A—C11A—H11A | 120.2 | C12B—C11B—H11B | 119.4 |
C11A—C12A—H12A | 120.1 | C11B—C12B—H12B | 119.9 |
C13A—C12A—C11A | 119.9 (4) | C13B—C12B—C11B | 120.1 (4) |
C13A—C12A—H12A | 120.1 | C13B—C12B—H12B | 119.9 |
C12A—C13A—H13A | 119.7 | C12B—C13B—H13B | 120.2 |
C12A—C13A—C14A | 120.6 (3) | C12B—C13B—C14B | 119.6 (3) |
C14A—C13A—H13A | 119.7 | C14B—C13B—H13B | 120.2 |
C13A—C14A—H14A | 120.0 | C13B—C14B—H14B | 119.7 |
C13A—C14A—C15A | 119.9 (4) | C13B—C14B—C15B | 120.7 (4) |
C15A—C14A—H14A | 120.0 | C15B—C14B—H14B | 119.7 |
C10A—C15A—H15A | 119.5 | C10B—C15B—C14B | 120.6 (4) |
C14A—C15A—C10A | 121.0 (3) | C10B—C15B—H15B | 119.7 |
C14A—C15A—H15A | 119.5 | C14B—C15B—H15B | 119.7 |
N2A—C16A—H16A | 109.0 | N2B—C16B—H16C | 108.7 |
N2A—C16A—H16B | 109.0 | N2B—C16B—H16D | 108.7 |
N2A—C16A—C17A | 112.97 (18) | N2B—C16B—C17B | 114.08 (18) |
H16A—C16A—H16B | 107.8 | H16C—C16B—H16D | 107.6 |
C17A—C16A—H16A | 109.0 | C17B—C16B—H16C | 108.7 |
C17A—C16A—H16B | 109.0 | C17B—C16B—H16D | 108.7 |
C18A—C17A—C16A | 120.2 (2) | C18B—C17B—C16B | 117.9 (2) |
C22A—C17A—C16A | 121.7 (2) | C22B—C17B—C16B | 123.27 (19) |
C22A—C17A—C18A | 118.1 (2) | C22B—C17B—C18B | 118.8 (2) |
C17A—C18A—H18A | 120.0 | C17B—C18B—H18B | 119.8 |
C17A—C18A—C19A | 120.1 (3) | C19B—C18B—C17B | 120.4 (3) |
C19A—C18A—H18A | 120.0 | C19B—C18B—H18B | 119.8 |
C18A—C19A—H19A | 119.6 | C18B—C19B—H19B | 119.7 |
C20A—C19A—C18A | 120.9 (3) | C20B—C19B—C18B | 120.6 (3) |
C20A—C19A—H19A | 119.6 | C20B—C19B—H19B | 119.7 |
C19A—C20A—H20A | 120.2 | C19B—C20B—H20B | 120.4 |
C19A—C20A—C21A | 119.6 (3) | C19B—C20B—C21B | 119.3 (3) |
C21A—C20A—H20A | 120.2 | C21B—C20B—H20B | 120.4 |
C20A—C21A—H21A | 120.0 | C20B—C21B—H21B | 119.6 |
C20A—C21A—C22A | 120.0 (3) | C20B—C21B—C22B | 120.9 (3) |
C22A—C21A—H21A | 120.0 | C22B—C21B—H21B | 119.6 |
C17A—C22A—C21A | 121.4 (3) | C17B—C22B—C21B | 120.0 (2) |
C17A—C22A—H22A | 119.3 | C17B—C22B—H22B | 120.0 |
C21A—C22A—H22A | 119.3 | C21B—C22B—H22B | 120.0 |
D—H···A | D—H | H···A | D···A | D—H···A |
C7A—H7A···O2Bi | 0.93 | 2.48 | 3.323 (3) | 151 |
C22A—H22A···O1Bi | 0.93 | 2.60 | 3.454 (3) | 154 |
C7B—H7B···O2A | 0.93 | 2.43 | 3.151 (3) | 135 |
C18B—H18B···O1A | 0.93 | 2.72 | 3.353 (3) | 126 |
Symmetry code: (i) x, −y+1/2, z+1/2. |
Footnotes
‡Laboratoire de Chimie Organique Hétérocyclique, Pôle de Compétences Pharmacochimie, Mohammed V University in Rabat, BP 1014, Avenue Ibn Batouta, Rabat, Morocco
Acknowledgements
JPJ acknowledges the NSF–MRI program (grant No. CHE-1039027) for funds to purchase the X-ray diffractometer.
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