organic compounds
(E)-N′-Benzylidene-2-phenylquinoline-4-carbohydrazide
aDepartment of Chemistry, Tulane University, New Orleans, LA 70118, USA, bChemistry and Environmental Division, Manchester Metropolitan University, Manchester M1 5GD, England, cChemistry Department, Faculty of Science, Minia University, 61519 El-Minia, Egypt, dDepartment of Physics, Faculty of Sciences, Erciyes University, 38039 Kayseri, Turkey, eKirkuk University, College of Education, Department of Chemistry, Kirkuk, Iraq, and fDepartment of Chemistry, College of Education, Tikrit University, Iraq
*Correspondence e-mail: shaabankamel@yahoo.com
In the title compound, C23H17N3O, there is a short intramolecular C—H⋯O contact present, and the conformation about the C=N bond is E. The phenyl and benzylidene rings make dihedral angles of 28.21 (15) and 37.65 (14)° with the mean plane of the quinoline moiety. In the crystal, molecules are linked by N—H⋯O and C—H⋯O hydrogen bonds, forming chains propagating along [001], with the O atom accepting three hydrogen bonds.
Keywords: crystal structure; quinoline; carbohydrazide; hydrogen bonding.
CCDC reference: 1507748
Structure description
It has been reported that quinoline derivatives serve as antagonists (Bennacef et al., 2007), analgesic agents (Gopalsamy & Pallai, 1997), 5HT3 antagonists (Anzini et al., 1995) and structural subunits of natural products (Sivaprasad et al., 2006). Among the compounds of a quinoline series, Atophan and its derivatives have shown a variety of biological effects (Muscia et al., 2008; Wang et al., 2009). Moreover, hydrazide-hydrazone compounds are found to be associated with various biological activities such as antimicrobial, anticonvulsant, analgesic, anti-inflammatory, anti-platelet, anti-tubercular and anti-tumour properties (Mohamed et al., 2015). As part of our studies in this area, we now report the of the title compound.
The molecular structure of the title compound is illustrated in Fig. 1. The quinoline moiety is slightly twisted as indicated by the dihedral angle of 2.27 (16)° between the C1–C6 and N1/C6–C9 rings. The phenyl (C10–C15) and benzylidene (C18–C23) rings make dihedral angles of 28.21 (15) and 37.65 (14)°, respectively, with the mean plane of the quinoline moiety. The conformation about the C17=N3 bond is E and there is a short C5—H5⋯O1 contact in the molecule (Table 1).
|
In the crystal, N2—H2A⋯O1i, C8—H8⋯O1i and C17—H17⋯O1i [symmetry code: (i) x, −y + 1, z − ] hydrogen bonds link the molecules into chains along the c-axis direction (Table 1 and Fig. 2).
Synthesis and crystallization
The title compound was prepared in 89% yield according to a reported procedure (Mohamed et al., 2016). Colourless needle-like crystals of the title compound were obtained by recrystallization from ethanol solution (m.p. 515–518 K).
Refinement
details are given in Table 2Structural data
CCDC reference: 1507748
https://doi.org/10.1107/S2414314616015443/su4080sup1.cif
contains datablocks global, I. DOI:Structure factors: contains datablock I. DOI: https://doi.org/10.1107/S2414314616015443/su4080Isup2.hkl
Supporting information file. DOI: https://doi.org/10.1107/S2414314616015443/su4080Isup3.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) and Mercury (Macrae et al., 2008); software used to prepare material for publication: SHELXTL (Sheldrick, 2008).C23H17N3O | F(000) = 368 |
Mr = 351.39 | Dx = 1.323 Mg m−3 |
Monoclinic, Pc | Cu Kα radiation, λ = 1.54178 Å |
a = 7.6704 (8) Å | Cell parameters from 5448 reflections |
b = 13.2898 (13) Å | θ = 3.3–72.3° |
c = 9.0627 (9) Å | µ = 0.66 mm−1 |
β = 107.220 (6)° | T = 150 K |
V = 882.42 (16) Å3 | Needles, colourless |
Z = 2 | 0.24 × 0.07 × 0.04 mm |
Bruker D8 VENTURE PHOTON 100 CMOS diffractometer | 2637 independent reflections |
Radiation source: INCOATEC IµS micro-focus source | 2394 reflections with I > 2σ(I) |
Mirror monochromator | Rint = 0.037 |
Detector resolution: 10.4167 pixels mm-1 | θmax = 72.3°, θmin = 3.3° |
ω scans | h = −9→8 |
Absorption correction: multi-scan (SADABS; Bruker, 2016) | k = −16→15 |
Tmin = 0.83, Tmax = 0.97 | l = −10→11 |
6668 measured reflections |
Refinement on F2 | Hydrogen site location: mixed |
Least-squares matrix: full | H atoms treated by a mixture of independent and constrained refinement |
R[F2 > 2σ(F2)] = 0.037 | w = 1/[σ2(Fo2) + (0.0333P)2 + 0.1673P] where P = (Fo2 + 2Fc2)/3 |
wR(F2) = 0.087 | (Δ/σ)max < 0.001 |
S = 1.07 | Δρmax = 0.16 e Å−3 |
2637 reflections | Δρmin = −0.16 e Å−3 |
250 parameters | Extinction correction: SHELXL2014 (Sheldrick, 2015b), Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4 |
2 restraints | Extinction coefficient: 0.0046 (8) |
Primary atom site location: structure-invariant direct methods | Absolute structure: Refined as an inversion twin |
Secondary atom site location: difference Fourier map | Absolute structure parameter: 0.2 (4) |
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. Refined as a 2-component inversion twin. |
x | y | z | Uiso*/Ueq | ||
O1 | 0.5328 (3) | 0.41857 (14) | 0.9098 (2) | 0.0351 (5) | |
N1 | 0.3365 (4) | 0.19467 (18) | 0.4307 (3) | 0.0312 (5) | |
N2 | 0.6135 (4) | 0.50398 (17) | 0.7228 (3) | 0.0296 (5) | |
H2A | 0.604 (5) | 0.510 (3) | 0.624 (4) | 0.045 (10)* | |
N3 | 0.6784 (3) | 0.58400 (17) | 0.8203 (3) | 0.0296 (5) | |
C1 | 0.4132 (4) | 0.1685 (2) | 0.5821 (3) | 0.0290 (6) | |
C2 | 0.4235 (4) | 0.0645 (2) | 0.6177 (3) | 0.0344 (7) | |
H2 | 0.3728 | 0.0170 | 0.5384 | 0.041* | |
C3 | 0.5054 (5) | 0.0318 (2) | 0.7645 (3) | 0.0361 (7) | |
H3 | 0.5112 | −0.0382 | 0.7874 | 0.043* | |
C4 | 0.5811 (5) | 0.1021 (2) | 0.8818 (3) | 0.0360 (7) | |
H4 | 0.6419 | 0.0790 | 0.9832 | 0.043* | |
C5 | 0.5688 (4) | 0.2030 (2) | 0.8526 (3) | 0.0331 (7) | |
H5 | 0.6186 | 0.2492 | 0.9343 | 0.040* | |
C6 | 0.4826 (4) | 0.2396 (2) | 0.7019 (3) | 0.0282 (6) | |
C7 | 0.4633 (4) | 0.3437 (2) | 0.6587 (3) | 0.0280 (6) | |
C8 | 0.3796 (4) | 0.3683 (2) | 0.5077 (3) | 0.0294 (6) | |
H8 | 0.3617 | 0.4370 | 0.4780 | 0.035* | |
C9 | 0.3195 (4) | 0.2915 (2) | 0.3955 (3) | 0.0296 (6) | |
C10 | 0.2341 (4) | 0.3167 (2) | 0.2296 (3) | 0.0318 (7) | |
C11 | 0.1402 (5) | 0.4069 (2) | 0.1854 (4) | 0.0373 (7) | |
H11 | 0.1363 | 0.4552 | 0.2616 | 0.045* | |
C12 | 0.0520 (5) | 0.4267 (3) | 0.0301 (4) | 0.0460 (8) | |
H12 | −0.0135 | 0.4877 | 0.0007 | 0.055* | |
C13 | 0.0603 (5) | 0.3570 (3) | −0.0810 (4) | 0.0479 (9) | |
H13 | −0.0009 | 0.3698 | −0.1868 | 0.058* | |
C14 | 0.1574 (6) | 0.2689 (3) | −0.0383 (4) | 0.0477 (9) | |
H14 | 0.1659 | 0.2224 | −0.1155 | 0.057* | |
C15 | 0.2429 (5) | 0.2475 (3) | 0.1164 (4) | 0.0400 (8) | |
H15 | 0.3071 | 0.1859 | 0.1449 | 0.048* | |
C16 | 0.5387 (4) | 0.4248 (2) | 0.7759 (3) | 0.0278 (6) | |
C17 | 0.7413 (4) | 0.6576 (2) | 0.7606 (3) | 0.0293 (6) | |
H17 | 0.7424 | 0.6530 | 0.6563 | 0.035* | |
C18 | 0.8117 (4) | 0.7491 (2) | 0.8492 (3) | 0.0278 (6) | |
C19 | 0.8098 (5) | 0.7608 (2) | 1.0015 (3) | 0.0349 (7) | |
H19 | 0.7640 | 0.7083 | 1.0510 | 0.042* | |
C20 | 0.8744 (5) | 0.8485 (2) | 1.0807 (4) | 0.0381 (7) | |
H20 | 0.8715 | 0.8565 | 1.1841 | 0.046* | |
C21 | 0.9431 (5) | 0.9247 (2) | 1.0102 (4) | 0.0381 (7) | |
H21 | 0.9869 | 0.9850 | 1.0653 | 0.046* | |
C22 | 0.9483 (5) | 0.9136 (2) | 0.8603 (4) | 0.0371 (7) | |
H22 | 0.9976 | 0.9655 | 0.8125 | 0.044* | |
C23 | 0.8806 (4) | 0.8257 (2) | 0.7794 (3) | 0.0328 (7) | |
H23 | 0.8818 | 0.8184 | 0.6755 | 0.039* |
U11 | U22 | U33 | U12 | U13 | U23 | |
O1 | 0.0532 (14) | 0.0323 (11) | 0.0202 (10) | 0.0008 (10) | 0.0114 (9) | −0.0002 (8) |
N1 | 0.0352 (15) | 0.0334 (13) | 0.0238 (12) | −0.0015 (11) | 0.0065 (10) | 0.0007 (10) |
N2 | 0.0400 (15) | 0.0293 (12) | 0.0177 (10) | −0.0012 (10) | 0.0058 (9) | −0.0007 (9) |
N3 | 0.0354 (15) | 0.0285 (12) | 0.0223 (11) | −0.0006 (10) | 0.0044 (10) | −0.0023 (9) |
C1 | 0.0334 (16) | 0.0288 (14) | 0.0237 (13) | 0.0004 (12) | 0.0070 (11) | −0.0004 (11) |
C2 | 0.0410 (19) | 0.0311 (15) | 0.0302 (16) | −0.0017 (14) | 0.0093 (14) | −0.0037 (12) |
C3 | 0.045 (2) | 0.0270 (15) | 0.0353 (16) | 0.0014 (13) | 0.0107 (14) | 0.0043 (12) |
C4 | 0.047 (2) | 0.0327 (16) | 0.0254 (15) | 0.0025 (14) | 0.0064 (13) | 0.0031 (11) |
C5 | 0.0429 (19) | 0.0321 (15) | 0.0218 (14) | 0.0003 (13) | 0.0058 (13) | 0.0000 (12) |
C6 | 0.0323 (17) | 0.0297 (15) | 0.0222 (13) | 0.0016 (12) | 0.0076 (11) | 0.0011 (11) |
C7 | 0.0326 (17) | 0.0275 (14) | 0.0233 (13) | 0.0008 (12) | 0.0075 (11) | −0.0006 (11) |
C8 | 0.0361 (17) | 0.0291 (14) | 0.0213 (13) | 0.0004 (12) | 0.0057 (11) | 0.0015 (11) |
C9 | 0.0308 (17) | 0.0338 (15) | 0.0229 (13) | −0.0011 (13) | 0.0059 (12) | −0.0002 (11) |
C10 | 0.0309 (17) | 0.0399 (17) | 0.0219 (14) | −0.0039 (13) | 0.0038 (12) | 0.0002 (12) |
C11 | 0.0402 (19) | 0.0422 (17) | 0.0254 (15) | 0.0001 (14) | 0.0034 (12) | 0.0025 (13) |
C12 | 0.044 (2) | 0.052 (2) | 0.0355 (18) | 0.0004 (16) | 0.0009 (14) | 0.0093 (15) |
C13 | 0.049 (2) | 0.065 (2) | 0.0227 (16) | −0.0093 (18) | 0.0005 (14) | 0.0049 (15) |
C14 | 0.054 (2) | 0.061 (2) | 0.0237 (15) | −0.0054 (18) | 0.0058 (14) | −0.0045 (15) |
C15 | 0.046 (2) | 0.0445 (18) | 0.0262 (15) | −0.0002 (15) | 0.0060 (13) | −0.0019 (13) |
C16 | 0.0352 (17) | 0.0272 (14) | 0.0192 (14) | 0.0029 (12) | 0.0049 (11) | 0.0004 (10) |
C17 | 0.0337 (17) | 0.0315 (15) | 0.0214 (13) | 0.0016 (12) | 0.0060 (11) | 0.0018 (11) |
C18 | 0.0279 (16) | 0.0308 (14) | 0.0220 (13) | 0.0019 (12) | 0.0033 (11) | 0.0000 (11) |
C19 | 0.0392 (18) | 0.0399 (17) | 0.0260 (15) | −0.0053 (14) | 0.0103 (13) | −0.0014 (12) |
C20 | 0.043 (2) | 0.0463 (18) | 0.0248 (14) | −0.0055 (15) | 0.0104 (13) | −0.0066 (13) |
C21 | 0.0415 (19) | 0.0350 (17) | 0.0349 (17) | −0.0007 (14) | 0.0068 (14) | −0.0077 (13) |
C22 | 0.0451 (19) | 0.0302 (15) | 0.0341 (16) | −0.0011 (13) | 0.0090 (13) | 0.0016 (12) |
C23 | 0.0398 (19) | 0.0330 (15) | 0.0236 (14) | 0.0033 (13) | 0.0065 (12) | 0.0022 (11) |
O1—C16 | 1.231 (3) | C10—C15 | 1.395 (4) |
N1—C9 | 1.324 (3) | C11—C12 | 1.394 (4) |
N1—C1 | 1.367 (4) | C11—H11 | 0.9500 |
N2—C16 | 1.353 (4) | C12—C13 | 1.382 (5) |
N2—N3 | 1.378 (3) | C12—H12 | 0.9500 |
N2—H2A | 0.88 (4) | C13—C14 | 1.381 (5) |
N3—C17 | 1.279 (4) | C13—H13 | 0.9500 |
C1—C2 | 1.416 (4) | C14—C15 | 1.390 (5) |
C1—C6 | 1.418 (4) | C14—H14 | 0.9500 |
C2—C3 | 1.363 (4) | C15—H15 | 0.9500 |
C2—H2 | 0.9500 | C17—C18 | 1.469 (4) |
C3—C4 | 1.406 (4) | C17—H17 | 0.9500 |
C3—H3 | 0.9500 | C18—C23 | 1.383 (4) |
C4—C5 | 1.365 (4) | C18—C19 | 1.393 (4) |
C4—H4 | 0.9500 | C19—C20 | 1.382 (4) |
C5—C6 | 1.416 (4) | C19—H19 | 0.9500 |
C5—H5 | 0.9500 | C20—C21 | 1.383 (5) |
C6—C7 | 1.434 (4) | C20—H20 | 0.9500 |
C7—C8 | 1.367 (4) | C21—C22 | 1.379 (4) |
C7—C16 | 1.504 (4) | C21—H21 | 0.9500 |
C8—C9 | 1.418 (4) | C22—C23 | 1.395 (4) |
C8—H8 | 0.9500 | C22—H22 | 0.9500 |
C9—C10 | 1.489 (4) | C23—H23 | 0.9500 |
C10—C11 | 1.395 (4) | ||
C9—N1—C1 | 118.1 (2) | C10—C11—H11 | 119.8 |
C16—N2—N3 | 118.8 (2) | C13—C12—C11 | 119.7 (3) |
C16—N2—H2A | 121 (2) | C13—C12—H12 | 120.1 |
N3—N2—H2A | 119 (2) | C11—C12—H12 | 120.1 |
C17—N3—N2 | 115.4 (2) | C14—C13—C12 | 120.1 (3) |
N1—C1—C2 | 117.1 (2) | C14—C13—H13 | 120.0 |
N1—C1—C6 | 123.4 (2) | C12—C13—H13 | 120.0 |
C2—C1—C6 | 119.5 (3) | C13—C14—C15 | 120.7 (3) |
C3—C2—C1 | 120.9 (3) | C13—C14—H14 | 119.7 |
C3—C2—H2 | 119.6 | C15—C14—H14 | 119.7 |
C1—C2—H2 | 119.6 | C14—C15—C10 | 119.7 (3) |
C2—C3—C4 | 119.6 (3) | C14—C15—H15 | 120.1 |
C2—C3—H3 | 120.2 | C10—C15—H15 | 120.1 |
C4—C3—H3 | 120.2 | O1—C16—N2 | 123.2 (3) |
C5—C4—C3 | 121.2 (3) | O1—C16—C7 | 122.0 (3) |
C5—C4—H4 | 119.4 | N2—C16—C7 | 114.9 (2) |
C3—C4—H4 | 119.4 | N3—C17—C18 | 121.7 (2) |
C4—C5—C6 | 120.6 (3) | N3—C17—H17 | 119.1 |
C4—C5—H5 | 119.7 | C18—C17—H17 | 119.1 |
C6—C5—H5 | 119.7 | C23—C18—C19 | 119.2 (3) |
C5—C6—C1 | 118.2 (2) | C23—C18—C17 | 119.2 (2) |
C5—C6—C7 | 125.1 (3) | C19—C18—C17 | 121.6 (3) |
C1—C6—C7 | 116.6 (2) | C20—C19—C18 | 120.1 (3) |
C8—C7—C6 | 118.9 (3) | C20—C19—H19 | 120.0 |
C8—C7—C16 | 120.2 (3) | C18—C19—H19 | 120.0 |
C6—C7—C16 | 120.8 (3) | C19—C20—C21 | 120.4 (3) |
C7—C8—C9 | 120.2 (3) | C19—C20—H20 | 119.8 |
C7—C8—H8 | 119.9 | C21—C20—H20 | 119.8 |
C9—C8—H8 | 119.9 | C22—C21—C20 | 120.2 (3) |
N1—C9—C8 | 122.6 (3) | C22—C21—H21 | 119.9 |
N1—C9—C10 | 116.4 (2) | C20—C21—H21 | 119.9 |
C8—C9—C10 | 121.0 (3) | C21—C22—C23 | 119.5 (3) |
C11—C10—C15 | 119.3 (3) | C21—C22—H22 | 120.2 |
C11—C10—C9 | 121.2 (3) | C23—C22—H22 | 120.2 |
C15—C10—C9 | 119.5 (3) | C18—C23—C22 | 120.6 (3) |
C12—C11—C10 | 120.4 (3) | C18—C23—H23 | 119.7 |
C12—C11—H11 | 119.8 | C22—C23—H23 | 119.7 |
C16—N2—N3—C17 | −177.6 (3) | C8—C9—C10—C15 | 154.4 (3) |
C9—N1—C1—C2 | 177.6 (3) | C15—C10—C11—C12 | 1.6 (5) |
C9—N1—C1—C6 | −2.9 (4) | C9—C10—C11—C12 | −176.2 (3) |
N1—C1—C2—C3 | 177.0 (3) | C10—C11—C12—C13 | −1.0 (5) |
C6—C1—C2—C3 | −2.5 (5) | C11—C12—C13—C14 | −0.8 (6) |
C1—C2—C3—C4 | −0.2 (5) | C12—C13—C14—C15 | 2.1 (6) |
C2—C3—C4—C5 | 2.2 (5) | C13—C14—C15—C10 | −1.5 (5) |
C3—C4—C5—C6 | −1.4 (5) | C11—C10—C15—C14 | −0.4 (5) |
C4—C5—C6—C1 | −1.4 (4) | C9—C10—C15—C14 | 177.5 (3) |
C4—C5—C6—C7 | −179.6 (3) | N3—N2—C16—O1 | −3.3 (4) |
N1—C1—C6—C5 | −176.2 (3) | N3—N2—C16—C7 | 177.0 (3) |
C2—C1—C6—C5 | 3.3 (4) | C8—C7—C16—O1 | 144.0 (3) |
N1—C1—C6—C7 | 2.2 (4) | C6—C7—C16—O1 | −37.9 (4) |
C2—C1—C6—C7 | −178.3 (3) | C8—C7—C16—N2 | −36.4 (4) |
C5—C6—C7—C8 | 178.8 (3) | C6—C7—C16—N2 | 141.7 (3) |
C1—C6—C7—C8 | 0.5 (4) | N2—N3—C17—C18 | 178.7 (3) |
C5—C6—C7—C16 | 0.6 (4) | N3—C17—C18—C23 | 179.0 (3) |
C1—C6—C7—C16 | −177.6 (3) | N3—C17—C18—C19 | −1.3 (5) |
C6—C7—C8—C9 | −2.4 (4) | C23—C18—C19—C20 | 0.7 (5) |
C16—C7—C8—C9 | 175.8 (3) | C17—C18—C19—C20 | −179.0 (3) |
C1—N1—C9—C8 | 0.9 (4) | C18—C19—C20—C21 | −0.7 (5) |
C1—N1—C9—C10 | −179.6 (3) | C19—C20—C21—C22 | −0.2 (5) |
C7—C8—C9—N1 | 1.8 (5) | C20—C21—C22—C23 | 1.2 (5) |
C7—C8—C9—C10 | −177.8 (3) | C19—C18—C23—C22 | 0.3 (5) |
N1—C9—C10—C11 | 152.7 (3) | C17—C18—C23—C22 | 179.9 (3) |
C8—C9—C10—C11 | −27.8 (4) | C21—C22—C23—C18 | −1.2 (5) |
N1—C9—C10—C15 | −25.2 (4) |
D—H···A | D—H | H···A | D···A | D—H···A |
C5—H5···O1 | 0.95 | 2.34 | 2.939 (3) | 121 |
N2—H2A···O1i | 0.88 (4) | 2.08 (4) | 2.907 (3) | 155 (4) |
C8—H8···O1i | 0.95 | 2.50 | 3.288 (3) | 140 |
C17—H17···O1i | 0.95 | 2.52 | 3.268 (3) | 136 |
Symmetry code: (i) x, −y+1, z−1/2. |
Acknowledgements
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.
References
Anzini, M., Cappelli, A., Vomero, S., Giorgi, G., Langer, T., Hamon, M., Merahi, N., Emerit, B. M., Cagnotto, A., Skorupska, M., Mennini, T. & Pinto, J. C. (1995). J. Med. Chem. 38, 2692–2704. CrossRef CAS PubMed Google Scholar
Bennacef, I., Perrio, C., Lasne, M. C. & Barré, L. (2007). J. Org. Chem. 72, 2161–2165. CrossRef PubMed CAS Google Scholar
Brandenburg, K. & Putz, H. (2012). DIAMOND. Crystal Impact GbR, Bonn, Germany. Google Scholar
Bruker (2016). APEX3, SAINT and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA. Google Scholar
Gopalsamy, A. & Pallai, P. V. (1997). Tetrahedron Lett. 38, 907–910. CrossRef CAS Google Scholar
Macrae, C. F., Bruno, I. J., Chisholm, J. A., Edgington, P. R., McCabe, P., Pidcock, E., Rodriguez-Monge, L., Taylor, R., van de Streek, J. & Wood, P. A. (2008). J. Appl. Cryst. 41, 466–470. Web of Science CSD CrossRef CAS IUCr Journals Google Scholar
Mohamed, S. K., Mague, J. T., Akkurt, M., Mohamed, A. F. & Albayati, M. R. (2015). Acta Cryst. E71, o957–o958. CSD CrossRef IUCr Journals Google Scholar
Mohamed, S. K., Mague, J. T., Akkurt, M., Mohamed, A. F. & Albayati, M. R. (2016). IUCrData, 1, x160662. Google Scholar
Muscia, G. C., Carnevale, J. P., Bollini, M. & Asís, S. E. (2008). J. Heterocycl. Chem. 45, 611–614. CrossRef CAS Google Scholar
Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. Web of Science CrossRef CAS IUCr Journals Google Scholar
Sheldrick, G. M. (2015a). Acta Cryst. A71, 3–8. Web of Science CrossRef IUCr Journals Google Scholar
Sheldrick, G. M. (2015b). Acta Cryst. C71, 3–8. Web of Science CrossRef IUCr Journals Google Scholar
Sivaprasad, G., Rajesh, R. & Perumal, P. T. (2006). Tetrahedron Lett. 47, 1783–1785. CrossRef CAS Google Scholar
Wang, L.-M., Hu, L., Chen, H.-J., Sui, Y.-Y. & Shen, W. (2009). J. Fluorine Chem. 130, 406–409. 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.