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

Journal logoIUCrDATA
ISSN: 2414-3146

1,4-Di­benzyl-6-chloro­quinoxaline-2,3(1H,4H)-dione

CROSSMARK_Color_square_no_text.svg

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

Edited by J. Simpson, University of Otago, New Zealand (Received 13 June 2017; accepted 16 June 2017; online 20 June 2017)

The title compound, C22H17ClN2O2, crystallizes with two independent mol­ecules (A and B) in the asymmetric unit. 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 ππ stacking inter­actions link the molecules into a three-dimensional network.

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

Structure description

Quinoxaline derivatives find use as anti­cancer (Noolvi et al., 2011[Noolvi, M. N., Patel, H. M., Bhardwaj, V. & Chauhan, A. (2011). Eur. J. Med. Chem. 46, 2327-2346.]), anti­diabetic (Bahekar et al., 2007[Bahekar, R. H., Jain, M. R., Gupta, A. A., Goel, A., Jadav, P. A., Patel, D. N., Prajapati, V. M. & Patel, P. R. (2007). Arch. Pharm. (Weinheim), 340, 359-366.]), anti­fungal (Xu and Fan, 2011[Xu, H. & Fan, L. L. (2011). Eur. J. Med. Chem. 46, 1919-1925.]), anti­viral (Caia et al., 2008[Caia, J. J., Zoua, J. P., Pana, X. Q. & Zhangb, W. (2008). Tetrahedron Lett. 49, 7386-7390.]) and anti-inflammatory agents (Yan et al., 2007[Yan, L., Liu, F. W., Dai, G. F. & Liu, H. M. (2007). Bioorg. Med. Chem. 17, 609-612.]). 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 asymmetric unit (Fig. 1[link]). 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[link]) within the asymmetric unit (Fig. 1[link]). Additional C—H⋯O hydrogen bonds, together with ππ 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[link]).

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A D—H H⋯A DA 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+{\script{1\over 2}}, z+{\script{1\over 2}}].
[Figure 1]
Figure 1
The mol­ecular structure of the title compound, showing the atom-numbering scheme for mol­ecules A and B, and 30% probability displacement ellipsoids for the non-H atoms. Dashed lines indicate weak C7B—H7B⋯O2A and C18B—H18B⋯O1A inter­molecular inter­actions within the asymmetric unit.
[Figure 2]
Figure 2
The packing of the title compound, viewed along the a axis. Dashed lines indicate inter­molecular C—H⋯O inter­actions. H atoms not involved in the packing have been omitted for clarity.

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 refinement details are summarized in Table 2[link].

Table 2
Experimental details

Crystal data
Chemical formula C22H17ClN2O2
Mr 376.82
Crystal system, space group Monoclinic, I2/a
Temperature (K) 293
a, b, c (Å) 29.2234 (4), 8.3076 (2), 31.0407 (5)
β (°) 101.859 (2)
V3) 7375.1 (2)
Z 16
Radiation type Cu Kα
μ (mm−1) 1.99
Crystal size (mm) 0.28 × 0.24 × 0.12
 
Data collection
Diffractometer Rigaku Oxford Diffraction
Absorption correction Multi-scan (CrysAlis PRO; Rigaku Oxford Diffraction, 2015[Rigaku Oxford Diffraction (2015). CrysAlis PRO. Rigaku Americas, The Woodlands, Texas, USA.])
Tmin, Tmax 0.500, 1.000
No. of measured, independent and observed [I > 2σ(I)] reflections 14412, 6996, 5661
Rint 0.022
(sin θ/λ)max−1) 0.614
 
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.053, 0.156, 1.04
No. of reflections 6996
No. of parameters 487
H-atom treatment H-atom parameters constrained
Δρmax, Δρmin (e Å−3) 0.73, −0.37
Computer programs: CrysAlis PRO (Rigaku Oxford Diffraction, 2015[Rigaku Oxford Diffraction (2015). CrysAlis PRO. Rigaku Americas, The Woodlands, Texas, USA.]), SHELXT (Sheldrick, 2015a[Sheldrick, G. M. (2015a). Acta Cryst. A71, 3-8.]), SHELXL2014 (Sheldrick, 2015b[Sheldrick, G. M. (2015b). Acta Cryst. C71, 3-8.]) and OLEX2 (Dolomanov et al., 2009[Dolomanov, O. V., Bourhis, L. J., Gildea, R. J., Howard, J. A. K. & Puschmann, H. (2009). J. Appl. Cryst. 42, 339-341.]).

Structural data


Computing details top

Data collection: CrysAlis PRO Rigaku Oxford Diffraction, 2015); cell refinement: 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).

1,4-Dibenzyl-6-chloroquinoxaline-2,3(1H,4H)-dione top
Crystal data top
C22H17ClN2O2F(000) = 3136
Mr = 376.82Dx = 1.358 Mg m3
Monoclinic, I2/aCu Kα radiation, λ = 1.54184 Å
a = 29.2234 (4) ÅCell parameters from 6649 reflections
b = 8.3076 (2) Åθ = 4.6–71.4°
c = 31.0407 (5) ŵ = 1.99 mm1
β = 101.859 (2)°T = 293 K
V = 7375.1 (2) Å3Prism, orange
Z = 160.28 × 0.24 × 0.12 mm
Data collection top
Rigaku Oxford Diffraction
diffractometer
6996 independent reflections
Radiation source: fine-focus sealed X-ray tube, Enhance (Cu) X-ray Source5661 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.022
Detector resolution: 16.0416 pixels mm-1θmax = 71.3°, θmin = 3.8°
ω scansh = 3525
Absorption correction: multi-scan
(CrysAlis PRO; Rigaku Oxford Diffraction, 2015)
k = 109
Tmin = 0.500, Tmax = 1.000l = 3738
14412 measured reflections
Refinement top
Refinement on F2Primary atom site location: dual
Least-squares matrix: fullHydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.053H-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 reflectionsΔρmax = 0.73 e Å3
487 parametersΔρmin = 0.37 e Å3
0 restraints
Special details top

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.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/Ueq
Cl1A0.62007 (2)0.06298 (9)0.71293 (2)0.0677 (2)
O1A0.53226 (7)0.1255 (3)0.47249 (6)0.0740 (6)
O2A0.46801 (6)0.3455 (3)0.48365 (6)0.0655 (5)
N1A0.55925 (6)0.1082 (2)0.54650 (6)0.0477 (4)
N2A0.48818 (6)0.3198 (2)0.55775 (6)0.0454 (4)
C1A0.53004 (8)0.1662 (3)0.50969 (7)0.0524 (6)
C2A0.49289 (8)0.2857 (3)0.51596 (7)0.0503 (5)
C3A0.51820 (7)0.2548 (2)0.59492 (7)0.0408 (4)
C4A0.55440 (7)0.1519 (3)0.58911 (7)0.0423 (4)
C5A0.58551 (7)0.0938 (3)0.62590 (7)0.0470 (5)
H5A0.61000.02680.62240.056*
C6A0.57996 (8)0.1356 (3)0.66737 (7)0.0481 (5)
C7A0.54401 (8)0.2333 (3)0.67408 (7)0.0472 (5)
H7A0.54060.25940.70240.057*
C8A0.51320 (7)0.2914 (3)0.63765 (7)0.0451 (5)
H8A0.48850.35650.64160.054*
C9A0.59406 (9)0.0137 (3)0.54046 (9)0.0590 (6)
H9AA0.58530.05810.51100.071*
H9AB0.59370.10070.56120.071*
C10A0.64278 (9)0.0527 (3)0.54688 (8)0.0578 (6)
C11A0.67930 (11)0.0200 (5)0.57570 (11)0.0882 (10)
H11A0.67380.11020.59170.106*
C12A0.72458 (12)0.0428 (8)0.58075 (13)0.1190 (18)
H12A0.74910.00360.60080.143*
C13A0.73264 (11)0.1720 (7)0.55627 (13)0.1114 (16)
H13A0.76280.21200.55920.134*
C14A0.69682 (11)0.2430 (5)0.52749 (12)0.0878 (10)
H14A0.70260.33150.51100.105*
C15A0.65210 (9)0.1837 (4)0.52278 (9)0.0649 (7)
H15A0.62780.23260.50310.078*
C16A0.45048 (8)0.4351 (3)0.56138 (8)0.0524 (5)
H16A0.45020.52080.54010.063*
H16B0.45720.48300.59050.063*
C17A0.40279 (8)0.3578 (3)0.55367 (8)0.0496 (5)
C18A0.37076 (10)0.3851 (4)0.51459 (9)0.0653 (7)
H18A0.37900.44890.49280.078*
C19A0.32639 (10)0.3172 (5)0.50810 (11)0.0825 (9)
H19A0.30510.33630.48190.099*
C20A0.31370 (10)0.2231 (4)0.53952 (13)0.0851 (10)
H20A0.28400.17730.53470.102*
C21A0.34496 (11)0.1960 (4)0.57839 (13)0.0856 (10)
H21A0.33630.13350.60020.103*
C22A0.38924 (9)0.2617 (4)0.58501 (10)0.0679 (7)
H22A0.41040.24070.61120.081*
Cl1B0.33081 (3)0.58144 (10)0.37621 (3)0.0797 (2)
O1B0.43598 (6)0.2708 (2)0.19629 (5)0.0610 (5)
O2B0.49943 (6)0.0979 (2)0.25341 (6)0.0627 (4)
N1B0.40704 (6)0.3788 (2)0.25221 (5)0.0427 (4)
N2B0.47554 (6)0.2118 (2)0.31145 (6)0.0429 (4)
C1B0.43687 (7)0.2823 (3)0.23545 (7)0.0445 (5)
C2B0.47303 (7)0.1879 (3)0.26761 (7)0.0457 (5)
C3B0.44279 (7)0.3067 (2)0.32762 (6)0.0405 (4)
C4B0.40761 (7)0.3855 (3)0.29761 (6)0.0401 (4)
C5B0.37306 (7)0.4698 (3)0.31310 (7)0.0468 (5)
H5B0.34890.51980.29350.056*
C6B0.37493 (9)0.4785 (3)0.35796 (8)0.0534 (6)
C7B0.41028 (9)0.4089 (3)0.38768 (7)0.0537 (6)
H7B0.41150.41900.41770.064*
C8B0.44431 (8)0.3231 (3)0.37248 (7)0.0484 (5)
H8B0.46860.27560.39260.058*
C9B0.37628 (8)0.4870 (3)0.22173 (7)0.0530 (5)
H9BA0.38770.49370.19460.064*
H9BB0.37820.59390.23450.064*
C10B0.32551 (8)0.4356 (3)0.21095 (7)0.0543 (6)
C11B0.31232 (10)0.2785 (4)0.20404 (11)0.0754 (8)
H11B0.33510.19910.20620.091*
C12B0.26533 (12)0.2348 (5)0.19378 (12)0.0946 (11)
H12B0.25700.12710.18930.113*
C13B0.23174 (11)0.3487 (7)0.19036 (12)0.1002 (13)
H13B0.20030.31960.18370.120*
C14B0.24408 (12)0.5056 (7)0.19666 (14)0.1053 (13)
H14B0.22100.58420.19390.126*
C15B0.29074 (11)0.5500 (5)0.20722 (12)0.0840 (9)
H15B0.29870.65800.21180.101*
C16B0.51314 (7)0.1264 (3)0.34172 (8)0.0487 (5)
H16C0.51940.02570.32820.058*
H16D0.50240.10070.36850.058*
C17B0.55802 (7)0.2199 (3)0.35376 (7)0.0421 (4)
C18B0.59036 (9)0.1716 (4)0.39071 (8)0.0608 (6)
H18B0.58270.09060.40860.073*
C19B0.63370 (9)0.2428 (4)0.40097 (10)0.0765 (9)
H19B0.65530.20840.42560.092*
C20B0.64540 (10)0.3633 (4)0.37538 (11)0.0771 (8)
H20B0.67500.40980.38220.093*
C21B0.61317 (10)0.4150 (4)0.33963 (11)0.0752 (8)
H21B0.62080.49870.32250.090*
C22B0.56949 (9)0.3443 (3)0.32867 (9)0.0597 (6)
H22B0.54790.38080.30430.072*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
Cl1A0.0533 (3)0.0909 (5)0.0550 (3)0.0014 (3)0.0025 (2)0.0022 (3)
O1A0.0727 (12)0.1090 (16)0.0461 (9)0.0143 (11)0.0256 (8)0.0145 (10)
O2A0.0555 (10)0.0907 (13)0.0486 (9)0.0118 (9)0.0072 (7)0.0121 (9)
N1A0.0455 (10)0.0541 (11)0.0483 (10)0.0116 (8)0.0207 (8)0.0102 (8)
N2A0.0446 (9)0.0484 (10)0.0447 (9)0.0100 (8)0.0126 (7)0.0000 (7)
C1A0.0488 (12)0.0684 (15)0.0434 (11)0.0221 (11)0.0171 (9)0.0073 (10)
C2A0.0458 (11)0.0622 (14)0.0445 (11)0.0206 (10)0.0131 (9)0.0012 (10)
C3A0.0384 (10)0.0422 (10)0.0437 (10)0.0133 (8)0.0131 (8)0.0026 (8)
C4A0.0417 (10)0.0447 (11)0.0438 (10)0.0138 (9)0.0162 (8)0.0058 (8)
C5A0.0407 (11)0.0494 (12)0.0545 (12)0.0074 (9)0.0178 (9)0.0061 (9)
C6A0.0423 (11)0.0549 (13)0.0471 (11)0.0126 (10)0.0095 (9)0.0019 (9)
C7A0.0468 (11)0.0556 (13)0.0430 (10)0.0129 (10)0.0180 (9)0.0093 (9)
C8A0.0415 (11)0.0485 (12)0.0488 (11)0.0077 (9)0.0173 (8)0.0051 (9)
C9A0.0696 (16)0.0543 (14)0.0594 (13)0.0053 (12)0.0275 (12)0.0142 (11)
C10A0.0566 (14)0.0690 (16)0.0523 (12)0.0075 (12)0.0218 (10)0.0145 (11)
C11A0.0734 (19)0.125 (3)0.0725 (18)0.035 (2)0.0303 (15)0.0056 (19)
C12A0.0602 (19)0.225 (6)0.074 (2)0.046 (3)0.0183 (16)0.006 (3)
C13A0.0471 (17)0.205 (5)0.088 (2)0.002 (2)0.0270 (16)0.031 (3)
C14A0.0553 (16)0.125 (3)0.092 (2)0.0153 (18)0.0360 (16)0.016 (2)
C15A0.0499 (13)0.0809 (18)0.0682 (15)0.0032 (13)0.0221 (11)0.0108 (14)
C16A0.0571 (13)0.0433 (12)0.0575 (13)0.0031 (10)0.0135 (10)0.0036 (10)
C17A0.0471 (12)0.0470 (12)0.0550 (12)0.0051 (10)0.0111 (9)0.0001 (10)
C18A0.0598 (15)0.0776 (18)0.0579 (14)0.0104 (13)0.0109 (11)0.0062 (13)
C19A0.0545 (16)0.108 (3)0.0772 (19)0.0088 (17)0.0048 (14)0.0033 (18)
C20A0.0480 (15)0.087 (2)0.115 (3)0.0072 (15)0.0055 (16)0.005 (2)
C21A0.0598 (17)0.090 (2)0.107 (2)0.0122 (16)0.0174 (16)0.0273 (19)
C22A0.0528 (14)0.0783 (18)0.0693 (16)0.0042 (13)0.0051 (12)0.0176 (14)
Cl1B0.0706 (4)0.0975 (6)0.0804 (5)0.0044 (4)0.0372 (3)0.0286 (4)
O1B0.0565 (9)0.0892 (13)0.0397 (8)0.0030 (9)0.0152 (7)0.0119 (8)
O2B0.0569 (9)0.0730 (11)0.0633 (10)0.0107 (9)0.0242 (8)0.0098 (9)
N1B0.0373 (8)0.0538 (10)0.0380 (8)0.0033 (8)0.0101 (6)0.0017 (7)
N2B0.0373 (9)0.0470 (10)0.0455 (9)0.0039 (7)0.0114 (7)0.0022 (7)
C1B0.0376 (10)0.0563 (12)0.0423 (10)0.0089 (9)0.0144 (8)0.0090 (9)
C2B0.0400 (10)0.0522 (12)0.0480 (11)0.0046 (9)0.0163 (8)0.0062 (9)
C3B0.0399 (10)0.0421 (10)0.0408 (10)0.0103 (8)0.0117 (8)0.0045 (8)
C4B0.0376 (10)0.0446 (11)0.0404 (10)0.0103 (8)0.0133 (8)0.0070 (8)
C5B0.0419 (11)0.0521 (12)0.0477 (11)0.0036 (10)0.0121 (9)0.0075 (9)
C6B0.0568 (13)0.0551 (13)0.0544 (12)0.0127 (11)0.0259 (10)0.0167 (10)
C7B0.0641 (14)0.0597 (14)0.0402 (11)0.0143 (11)0.0174 (10)0.0090 (10)
C8B0.0537 (12)0.0506 (12)0.0413 (10)0.0104 (10)0.0104 (9)0.0014 (9)
C9B0.0514 (12)0.0617 (14)0.0475 (11)0.0005 (11)0.0136 (9)0.0070 (10)
C10B0.0468 (12)0.0740 (16)0.0419 (11)0.0031 (11)0.0084 (9)0.0051 (10)
C11B0.0551 (15)0.081 (2)0.086 (2)0.0020 (14)0.0062 (14)0.0088 (16)
C12B0.066 (2)0.114 (3)0.098 (2)0.027 (2)0.0026 (17)0.002 (2)
C13B0.0479 (17)0.161 (4)0.087 (2)0.012 (2)0.0027 (14)0.019 (3)
C14B0.0521 (18)0.145 (4)0.115 (3)0.027 (2)0.0084 (17)0.020 (3)
C15B0.0609 (17)0.091 (2)0.096 (2)0.0137 (16)0.0063 (15)0.0105 (18)
C16B0.0452 (11)0.0469 (12)0.0549 (12)0.0024 (9)0.0128 (9)0.0079 (10)
C17B0.0408 (10)0.0445 (11)0.0427 (10)0.0037 (9)0.0124 (8)0.0012 (8)
C18B0.0523 (13)0.0787 (17)0.0517 (12)0.0067 (12)0.0113 (10)0.0151 (12)
C19B0.0472 (14)0.110 (2)0.0658 (16)0.0030 (15)0.0046 (12)0.0118 (16)
C20B0.0448 (14)0.089 (2)0.092 (2)0.0110 (14)0.0015 (13)0.0024 (17)
C21B0.0602 (16)0.0688 (18)0.094 (2)0.0184 (14)0.0098 (14)0.0180 (15)
C22B0.0526 (13)0.0600 (14)0.0611 (14)0.0087 (11)0.0009 (10)0.0151 (12)
Geometric parameters (Å, º) top
Cl1A—C6A1.748 (2)Cl1B—C6B1.737 (2)
O1A—C1A1.218 (3)O1B—C1B1.214 (3)
O2A—C2A1.217 (3)O2B—C2B1.220 (3)
N1A—C1A1.366 (3)N1B—C1B1.364 (3)
N1A—C4A1.407 (3)N1B—C4B1.407 (2)
N1A—C9A1.474 (3)N1B—C9B1.470 (3)
N2A—C2A1.362 (3)N2B—C2B1.362 (3)
N2A—C3A1.406 (3)N2B—C3B1.409 (3)
N2A—C16A1.482 (3)N2B—C16B1.472 (3)
C1A—C2A1.513 (4)C1B—C2B1.515 (3)
C3A—C4A1.400 (3)C3B—C4B1.400 (3)
C3A—C8A1.398 (3)C3B—C8B1.391 (3)
C4A—C5A1.392 (3)C4B—C5B1.393 (3)
C5A—H5A0.9300C5B—H5B0.9300
C5A—C6A1.375 (3)C5B—C6B1.384 (3)
C6A—C7A1.377 (3)C6B—C7B1.364 (4)
C7A—H7A0.9300C7B—H7B0.9300
C7A—C8A1.380 (3)C7B—C8B1.383 (3)
C8A—H8A0.9300C8B—H8B0.9300
C9A—H9AA0.9700C9B—H9BA0.9700
C9A—H9AB0.9700C9B—H9BB0.9700
C9A—C10A1.502 (4)C9B—C10B1.514 (3)
C10A—C11A1.383 (4)C10B—C11B1.365 (4)
C10A—C15A1.379 (4)C10B—C15B1.379 (4)
C11A—H11A0.9300C11B—H11B0.9300
C11A—C12A1.401 (6)C11B—C12B1.392 (4)
C12A—H12A0.9300C12B—H12B0.9300
C12A—C13A1.363 (7)C12B—C13B1.351 (6)
C13A—H13A0.9300C13B—H13B0.9300
C13A—C14A1.363 (6)C13B—C14B1.356 (6)
C14A—H14A0.9300C14B—H14B0.9300
C14A—C15A1.376 (4)C14B—C15B1.385 (5)
C15A—H15A0.9300C15B—H15B0.9300
C16A—H16A0.9700C16B—H16C0.9700
C16A—H16B0.9700C16B—H16D0.9700
C16A—C17A1.508 (3)C16B—C17B1.504 (3)
C17A—C18A1.390 (3)C17B—C18B1.387 (3)
C17A—C22A1.378 (4)C17B—C22B1.376 (3)
C18A—H18A0.9300C18B—H18B0.9300
C18A—C19A1.390 (4)C18B—C19B1.374 (4)
C19A—H19A0.9300C19B—H19B0.9300
C19A—C20A1.359 (5)C19B—C20B1.365 (5)
C20A—H20A0.9300C20B—H20B0.9300
C20A—C21A1.374 (5)C20B—C21B1.369 (4)
C21A—H21A0.9300C21B—H21B0.9300
C21A—C22A1.380 (4)C21B—C22B1.382 (4)
C22A—H22A0.9300C22B—H22B0.9300
C1A—N1A—C4A121.9 (2)C1B—N1B—C4B121.89 (18)
C1A—N1A—C9A117.70 (19)C1B—N1B—C9B117.92 (18)
C4A—N1A—C9A120.2 (2)C4B—N1B—C9B120.02 (18)
C2A—N2A—C3A122.26 (19)C2B—N2B—C3B122.42 (18)
C2A—N2A—C16A115.41 (19)C2B—N2B—C16B116.56 (18)
C3A—N2A—C16A122.29 (18)C3B—N2B—C16B120.96 (17)
O1A—C1A—N1A123.3 (2)O1B—C1B—N1B123.0 (2)
O1A—C1A—C2A118.9 (2)O1B—C1B—C2B119.2 (2)
N1A—C1A—C2A117.75 (19)N1B—C1B—C2B117.83 (18)
O2A—C2A—N2A122.7 (2)O2B—C2B—N2B122.8 (2)
O2A—C2A—C1A119.0 (2)O2B—C2B—C1B119.1 (2)
N2A—C2A—C1A118.3 (2)N2B—C2B—C1B118.04 (18)
C4A—C3A—N2A119.30 (18)C4B—C3B—N2B118.95 (18)
C8A—C3A—N2A121.74 (19)C8B—C3B—N2B121.8 (2)
C8A—C3A—C4A118.96 (19)C8B—C3B—C4B119.2 (2)
C3A—C4A—N1A120.23 (19)C3B—C4B—N1B120.27 (18)
C5A—C4A—N1A120.5 (2)C5B—C4B—N1B120.35 (19)
C5A—C4A—C3A119.31 (19)C5B—C4B—C3B119.38 (19)
C4A—C5A—H5A120.1C4B—C5B—H5B120.3
C6A—C5A—C4A119.9 (2)C6B—C5B—C4B119.5 (2)
C6A—C5A—H5A120.1C6B—C5B—H5B120.3
C5A—C6A—Cl1A118.80 (18)C5B—C6B—Cl1B118.4 (2)
C5A—C6A—C7A122.1 (2)C7B—C6B—Cl1B119.86 (18)
C7A—C6A—Cl1A119.12 (17)C7B—C6B—C5B121.7 (2)
C6A—C7A—H7A120.9C6B—C7B—H7B120.5
C6A—C7A—C8A118.2 (2)C6B—C7B—C8B119.0 (2)
C8A—C7A—H7A120.9C8B—C7B—H7B120.5
C3A—C8A—H8A119.2C3B—C8B—H8B119.5
C7A—C8A—C3A121.6 (2)C7B—C8B—C3B121.0 (2)
C7A—C8A—H8A119.2C7B—C8B—H8B119.5
N1A—C9A—H9AA109.0N1B—C9B—H9BA108.7
N1A—C9A—H9AB109.0N1B—C9B—H9BB108.7
N1A—C9A—C10A113.0 (2)N1B—C9B—C10B114.3 (2)
H9AA—C9A—H9AB107.8H9BA—C9B—H9BB107.6
C10A—C9A—H9AA109.0C10B—C9B—H9BA108.7
C10A—C9A—H9AB109.0C10B—C9B—H9BB108.7
C11A—C10A—C9A120.7 (3)C11B—C10B—C9B122.5 (2)
C15A—C10A—C9A120.4 (2)C11B—C10B—C15B117.8 (3)
C15A—C10A—C11A118.9 (3)C15B—C10B—C9B119.7 (3)
C10A—C11A—H11A120.2C10B—C11B—H11B119.4
C10A—C11A—C12A119.7 (4)C10B—C11B—C12B121.2 (3)
C12A—C11A—H11A120.2C12B—C11B—H11B119.4
C11A—C12A—H12A120.1C11B—C12B—H12B119.9
C13A—C12A—C11A119.9 (4)C13B—C12B—C11B120.1 (4)
C13A—C12A—H12A120.1C13B—C12B—H12B119.9
C12A—C13A—H13A119.7C12B—C13B—H13B120.2
C12A—C13A—C14A120.6 (3)C12B—C13B—C14B119.6 (3)
C14A—C13A—H13A119.7C14B—C13B—H13B120.2
C13A—C14A—H14A120.0C13B—C14B—H14B119.7
C13A—C14A—C15A119.9 (4)C13B—C14B—C15B120.7 (4)
C15A—C14A—H14A120.0C15B—C14B—H14B119.7
C10A—C15A—H15A119.5C10B—C15B—C14B120.6 (4)
C14A—C15A—C10A121.0 (3)C10B—C15B—H15B119.7
C14A—C15A—H15A119.5C14B—C15B—H15B119.7
N2A—C16A—H16A109.0N2B—C16B—H16C108.7
N2A—C16A—H16B109.0N2B—C16B—H16D108.7
N2A—C16A—C17A112.97 (18)N2B—C16B—C17B114.08 (18)
H16A—C16A—H16B107.8H16C—C16B—H16D107.6
C17A—C16A—H16A109.0C17B—C16B—H16C108.7
C17A—C16A—H16B109.0C17B—C16B—H16D108.7
C18A—C17A—C16A120.2 (2)C18B—C17B—C16B117.9 (2)
C22A—C17A—C16A121.7 (2)C22B—C17B—C16B123.27 (19)
C22A—C17A—C18A118.1 (2)C22B—C17B—C18B118.8 (2)
C17A—C18A—H18A120.0C17B—C18B—H18B119.8
C17A—C18A—C19A120.1 (3)C19B—C18B—C17B120.4 (3)
C19A—C18A—H18A120.0C19B—C18B—H18B119.8
C18A—C19A—H19A119.6C18B—C19B—H19B119.7
C20A—C19A—C18A120.9 (3)C20B—C19B—C18B120.6 (3)
C20A—C19A—H19A119.6C20B—C19B—H19B119.7
C19A—C20A—H20A120.2C19B—C20B—H20B120.4
C19A—C20A—C21A119.6 (3)C19B—C20B—C21B119.3 (3)
C21A—C20A—H20A120.2C21B—C20B—H20B120.4
C20A—C21A—H21A120.0C20B—C21B—H21B119.6
C20A—C21A—C22A120.0 (3)C20B—C21B—C22B120.9 (3)
C22A—C21A—H21A120.0C22B—C21B—H21B119.6
C17A—C22A—C21A121.4 (3)C17B—C22B—C21B120.0 (2)
C17A—C22A—H22A119.3C17B—C22B—H22B120.0
C21A—C22A—H22A119.3C21B—C22B—H22B120.0
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
C7A—H7A···O2Bi0.932.483.323 (3)151
C22A—H22A···O1Bi0.932.603.454 (3)154
C7B—H7B···O2A0.932.433.151 (3)135
C18B—H18B···O1A0.932.723.353 (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.

References

First citationBahekar, R. H., Jain, M. R., Gupta, A. A., Goel, A., Jadav, P. A., Patel, D. N., Prajapati, V. M. & Patel, P. R. (2007). Arch. Pharm. (Weinheim), 340, 359–366.  CrossRef PubMed CAS Google Scholar
First citationCaia, J. J., Zoua, J. P., Pana, X. Q. & Zhangb, W. (2008). Tetrahedron Lett. 49, 7386–7390.  Google Scholar
First citationDolomanov, O. V., Bourhis, L. J., Gildea, R. J., Howard, J. A. K. & Puschmann, H. (2009). J. Appl. Cryst. 42, 339–341.  Web of Science CrossRef CAS IUCr Journals Google Scholar
First citationNoolvi, M. N., Patel, H. M., Bhardwaj, V. & Chauhan, A. (2011). Eur. J. Med. Chem. 46, 2327–2346.  Web of Science CrossRef CAS PubMed Google Scholar
First citationRigaku Oxford Diffraction (2015). CrysAlis PRO. Rigaku Americas, The Woodlands, Texas, USA.  Google Scholar
First citationSheldrick, G. M. (2015a). Acta Cryst. A71, 3–8.  Web of Science CrossRef IUCr Journals Google Scholar
First citationSheldrick, G. M. (2015b). Acta Cryst. C71, 3–8.  Web of Science CrossRef IUCr Journals Google Scholar
First citationXu, H. & Fan, L. L. (2011). Eur. J. Med. Chem. 46, 1919–1925.  CrossRef CAS PubMed Google Scholar
First citationYan, L., Liu, F. W., Dai, G. F. & Liu, H. M. (2007). Bioorg. Med. Chem. 17, 609–612.  CrossRef CAS Google Scholar

This is an open-access article distributed under the terms of the Creative Commons Attribution (CC-BY) Licence, which permits unrestricted use, distribution, and reproduction in any medium, provided the original authors and source are cited.

Journal logoIUCrDATA
ISSN: 2414-3146
Follow IUCr Journals
Sign up for e-alerts
Follow IUCr on Twitter
Follow us on facebook
Sign up for RSS feeds