organic compounds
1-{2-Anilino-4-methyl-5-[5-methyl-1-(4-methylphenyl)-1H-1,2,3-triazole-4-carbonyl]thiophen-3-yl}ethanone
aCornea Research Chair, Department of Optometry, College of Applied Medical Sciences, King Saud University, PO Box 10219, Riyadh 11433, Saudi Arabia, bDepartment of Chemistry, College of Science and Humanities, Shaqra University, Duwadimi, Saudi Arabia, cApplied Organic Chemistry Department, National Research Centre, Dokki, Giza, Egypt, dChemistry Department, Faculty of Science, Jazan University, Jazan 2079, Saudi Arabia, eChemical Industries Division, National Research Centre, Dokki 12622, Giza, Egypt, fChemistry Department, Faculty of Science, Damietta University, Egypt, and gSchool of Chemistry, Cardiff University, Main Building, Park Place, Cardiff CF10 3AT, UK
*Correspondence e-mail: gelhiti@ksu.edu.sa
In the title compound, C24H22N4O2S, the dihedral angle between the triazole and thiophene rings is 4.83 (14)°. The dihedral angles between the triazole and tolyl rings and between the thiophene and phenyl rings are 48.42 (16) and 9.23 (13)°, respectively. An intramolecular N—H⋯O hydrogen bond closes an S(6) loop. In the crystal, molecules are stacked parallel to the a-axis direction with weak π–π interactions between adjacent thiophenyl and triazolyl groups within the stack [centroid–centroid separation = 3.9811 (16) Å].
Keywords: crystal structure; 1,2,3-triazole; thiophene.
CCDC reference: 1828289
Structure description
Heterocycles containing 1,2,3-triazole and thiophene moieties have a wide range of applications (Dheer et al., 2017; Jiang & Kuang, 2013; Li et al., 2016; Mancuso & Gabriele, 2014; Shafran et al., 2008; Yamada et al., 2018). As part of our studies in this area, we now describe the of the title compound.
The 24H22N4O2S (Fig. 1). The dihedral angle between the triazole and thiophene rings is 4.83 (14)°. The dihedral angles between the triazole and tolyl rings and between the thiophene and phenyl rings are 48.42 (16) and 9.23 (13)°, respectively. An intramolecular N4—H4A⋯O2 hydrogen bond closes an S(6) loop (Table 1). In the crystal, the molecules are stacked parallel to the a-axis direction with weak π–π interactions [centroid–centroid separation = 3.9811 (16) Å] between adjacent thiophenyl and triazolyl groups within the stack (Figs. 2 and 3).
consists of one molecule of C
|
Synthesis and crystallization
The title compound was obtained using a literature procedure (Mohamed et al., 2017). Yellow plates were recrystallized from dimethylformamide soluton in 74% yield; m.p. 222–224°C.
Refinement
Crystal data, data collection and structure .
details are summarized in Table 2Structural data
CCDC reference: 1828289
https://doi.org/10.1107/S2414314618004029/hb4214sup1.cif
contains datablock I. DOI:Structure factors: contains datablock I. DOI: https://doi.org/10.1107/S2414314618004029/hb4214Isup2.hkl
Supporting information file. DOI: https://doi.org/10.1107/S2414314618004029/hb4214Isup3.cml
Data collection: CrysAlis PRO (Rigaku OD, 2015); cell
CrysAlis PRO (Rigaku OD, 2015); data reduction: CrysAlis PRO (Rigaku OD, 2015); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL2018 (Sheldrick, 2015); molecular graphics: ORTEP-3 for Windows (Farrugia, 2012); software used to prepare material for publication: WinGX (Farrugia, 2012) and CHEMDRAW Ultra (Cambridge Soft, 2001).C24H22N4O2S | F(000) = 904 |
Mr = 430.51 | Dx = 1.332 Mg m−3 |
Monoclinic, P21/c | Mo Kα radiation, λ = 0.71073 Å |
a = 6.2938 (5) Å | Cell parameters from 3306 reflections |
b = 10.9254 (9) Å | θ = 3.7–25.6° |
c = 31.229 (4) Å | µ = 0.18 mm−1 |
β = 90.221 (8)° | T = 296 K |
V = 2147.4 (4) Å3 | Plate, yellow |
Z = 4 | 0.60 × 0.15 × 0.06 mm |
Rigaku Oxford Diffraction SuperNova, Dual, Cu at zero, Atlas diffractometer | 2925 reflections with I > 2σ(I) |
ω scans | Rint = 0.058 |
Absorption correction: gaussian (CrysAlis PRO; Rigaku OD, 2015) | θmax = 30.0°, θmin = 3.5° |
Tmin = 0.993, Tmax = 0.998 | h = −8→7 |
18565 measured reflections | k = −14→15 |
5355 independent reflections | l = −42→36 |
Refinement on F2 | Primary atom site location: structure-invariant direct methods |
Least-squares matrix: full | Hydrogen site location: inferred from neighbouring sites |
R[F2 > 2σ(F2)] = 0.061 | H-atom parameters constrained |
wR(F2) = 0.150 | w = 1/[σ2(Fo2) + (0.044P)2 + 0.7067P] where P = (Fo2 + 2Fc2)/3 |
S = 1.03 | (Δ/σ)max < 0.001 |
5355 reflections | Δρmax = 0.17 e Å−3 |
284 parameters | Δρmin = −0.23 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. |
Refinement. All hydrogen atoms were placed in calculated positions and refined using a riding model. Aromatic C—H distances were set to 0.93\%A and their U(iso) set to 1.2 times the Ueq for the atoms to which they are bonded. Methyl groups were allowed to rotate about the C—C bond and C—H distances were set to 0.96\%A with U(iso) set to 1.5 times the Ueq for the C atoms to which they are bonded. The N—H bond was set to 0.86 Å and Uiso(H) set to 1.2 times Ueq (N). |
x | y | z | Uiso*/Ueq | ||
C1 | 1.0844 (6) | 0.4701 (5) | 0.30830 (15) | 0.147 (2) | |
H1A | 1.108519 | 0.393718 | 0.322722 | 0.221* | |
H1B | 1.052358 | 0.532344 | 0.328987 | 0.221* | |
H1C | 1.209563 | 0.492748 | 0.292718 | 0.221* | |
C2 | 0.8982 (5) | 0.4565 (5) | 0.27729 (13) | 0.0941 (12) | |
C3 | 0.8627 (5) | 0.5421 (4) | 0.24562 (13) | 0.0975 (13) | |
H3 | 0.951860 | 0.609790 | 0.243839 | 0.117* | |
C4 | 0.6972 (5) | 0.5300 (3) | 0.21623 (11) | 0.0781 (9) | |
H4 | 0.675965 | 0.588220 | 0.194905 | 0.094* | |
C5 | 0.5657 (4) | 0.4299 (3) | 0.21949 (10) | 0.0599 (7) | |
C6 | 0.5955 (5) | 0.3451 (3) | 0.25146 (11) | 0.0759 (9) | |
H6 | 0.503424 | 0.278965 | 0.254083 | 0.091* | |
C7 | 0.7638 (5) | 0.3589 (4) | 0.27974 (12) | 0.0909 (11) | |
H7 | 0.785641 | 0.300306 | 0.300890 | 0.109* | |
C8 | 0.4691 (4) | 0.1979 (2) | 0.16645 (10) | 0.0658 (8) | |
H8A | 0.610090 | 0.213815 | 0.176877 | 0.099* | |
H8B | 0.476556 | 0.165169 | 0.137965 | 0.099* | |
H8C | 0.400558 | 0.139825 | 0.184882 | 0.099* | |
C9 | 0.3448 (4) | 0.3143 (2) | 0.16587 (9) | 0.0506 (6) | |
C10 | 0.1699 (4) | 0.3507 (2) | 0.14252 (9) | 0.0499 (6) | |
C11 | 0.0454 (4) | 0.2756 (2) | 0.11238 (9) | 0.0544 (7) | |
C12 | −0.1452 (4) | 0.3207 (2) | 0.09090 (8) | 0.0485 (6) | |
C13 | −0.2792 (4) | 0.2570 (2) | 0.06385 (8) | 0.0483 (6) | |
C14 | −0.4553 (4) | 0.3276 (2) | 0.04919 (8) | 0.0468 (6) | |
C15 | −0.4475 (4) | 0.4479 (2) | 0.06554 (8) | 0.0462 (6) | |
C16 | −0.2392 (5) | 0.1256 (2) | 0.05188 (12) | 0.0774 (10) | |
H16A | −0.099602 | 0.102095 | 0.061276 | 0.116* | |
H16B | −0.249296 | 0.116666 | 0.021362 | 0.116* | |
H16C | −0.343038 | 0.074289 | 0.065371 | 0.116* | |
C17 | −0.6339 (4) | 0.2894 (2) | 0.02206 (9) | 0.0535 (7) | |
C18 | −0.6614 (4) | 0.1593 (2) | 0.00682 (11) | 0.0708 (8) | |
H18A | −0.792619 | 0.152184 | −0.008755 | 0.106* | |
H18B | −0.663793 | 0.105202 | 0.031040 | 0.106* | |
H18C | −0.545254 | 0.137656 | −0.011533 | 0.106* | |
C19 | −0.6221 (4) | 0.6541 (2) | 0.07278 (8) | 0.0483 (6) | |
C20 | −0.8126 (4) | 0.7101 (2) | 0.06251 (10) | 0.0622 (8) | |
H20 | −0.914276 | 0.668419 | 0.046483 | 0.075* | |
C21 | −0.8514 (4) | 0.8282 (3) | 0.07617 (11) | 0.0720 (9) | |
H21 | −0.979294 | 0.865810 | 0.069033 | 0.086* | |
C22 | −0.7045 (5) | 0.8909 (2) | 0.10002 (10) | 0.0691 (8) | |
H22 | −0.732975 | 0.969785 | 0.109568 | 0.083* | |
C23 | −0.5159 (5) | 0.8359 (2) | 0.10959 (10) | 0.0708 (9) | |
H23 | −0.414335 | 0.878505 | 0.125337 | 0.085* | |
C24 | −0.4730 (4) | 0.7178 (2) | 0.09628 (10) | 0.0653 (8) | |
H24 | −0.343707 | 0.681488 | 0.103168 | 0.078* | |
N1 | 0.3972 (3) | 0.4139 (2) | 0.18886 (7) | 0.0557 (6) | |
N2 | 0.2643 (4) | 0.5101 (2) | 0.17970 (8) | 0.0674 (7) | |
N3 | 0.1272 (3) | 0.4702 (2) | 0.15169 (8) | 0.0614 (6) | |
N4 | −0.5960 (3) | 0.53417 (17) | 0.05747 (7) | 0.0519 (5) | |
H4A | −0.692643 | 0.511443 | 0.039618 | 0.062* | |
O1 | 0.1094 (3) | 0.16977 (17) | 0.10657 (8) | 0.0850 (7) | |
O2 | −0.7730 (3) | 0.36351 (17) | 0.01127 (7) | 0.0678 (6) | |
S1 | −0.23163 (9) | 0.47131 (5) | 0.09830 (2) | 0.0503 (2) |
U11 | U22 | U33 | U12 | U13 | U23 | |
C1 | 0.070 (2) | 0.251 (6) | 0.121 (4) | −0.001 (3) | −0.031 (2) | −0.071 (4) |
C2 | 0.0587 (18) | 0.149 (4) | 0.075 (3) | −0.004 (2) | −0.0041 (17) | −0.040 (3) |
C3 | 0.075 (2) | 0.134 (3) | 0.084 (3) | −0.040 (2) | 0.018 (2) | −0.044 (3) |
C4 | 0.0793 (19) | 0.090 (2) | 0.066 (2) | −0.0208 (18) | 0.0045 (16) | −0.0187 (18) |
C5 | 0.0502 (14) | 0.0720 (18) | 0.058 (2) | −0.0035 (14) | 0.0001 (13) | −0.0134 (16) |
C6 | 0.0725 (18) | 0.087 (2) | 0.068 (2) | −0.0062 (17) | −0.0122 (16) | −0.0021 (19) |
C7 | 0.084 (2) | 0.115 (3) | 0.074 (3) | 0.014 (2) | −0.0183 (19) | −0.013 (2) |
C8 | 0.0622 (16) | 0.0630 (17) | 0.072 (2) | 0.0132 (14) | −0.0087 (14) | −0.0003 (15) |
C9 | 0.0525 (14) | 0.0490 (14) | 0.0504 (17) | 0.0010 (12) | 0.0005 (11) | −0.0017 (12) |
C10 | 0.0511 (13) | 0.0455 (14) | 0.0529 (17) | 0.0047 (11) | −0.0030 (11) | −0.0017 (12) |
C11 | 0.0641 (15) | 0.0423 (14) | 0.0567 (19) | 0.0090 (12) | −0.0034 (13) | −0.0030 (12) |
C12 | 0.0531 (13) | 0.0364 (12) | 0.0558 (18) | 0.0043 (11) | −0.0017 (12) | 0.0002 (12) |
C13 | 0.0536 (13) | 0.0386 (12) | 0.0528 (17) | 0.0000 (11) | 0.0009 (11) | −0.0038 (11) |
C14 | 0.0504 (13) | 0.0383 (12) | 0.0518 (17) | −0.0019 (11) | 0.0007 (11) | −0.0044 (11) |
C15 | 0.0492 (13) | 0.0400 (13) | 0.0494 (17) | −0.0005 (11) | −0.0014 (11) | 0.0011 (11) |
C16 | 0.0778 (19) | 0.0449 (15) | 0.109 (3) | 0.0109 (14) | −0.0271 (18) | −0.0228 (17) |
C17 | 0.0557 (14) | 0.0493 (15) | 0.0555 (18) | −0.0039 (13) | 0.0006 (12) | −0.0054 (13) |
C18 | 0.0740 (18) | 0.0581 (17) | 0.080 (2) | −0.0079 (14) | −0.0177 (16) | −0.0171 (16) |
C19 | 0.0536 (14) | 0.0363 (12) | 0.0550 (17) | 0.0052 (11) | −0.0055 (11) | −0.0012 (11) |
C20 | 0.0556 (15) | 0.0513 (15) | 0.080 (2) | 0.0044 (13) | −0.0134 (14) | −0.0078 (14) |
C21 | 0.0632 (17) | 0.0551 (17) | 0.097 (3) | 0.0184 (14) | −0.0155 (16) | −0.0080 (17) |
C22 | 0.086 (2) | 0.0438 (14) | 0.078 (2) | 0.0183 (15) | −0.0109 (16) | −0.0106 (15) |
C23 | 0.084 (2) | 0.0466 (15) | 0.081 (2) | 0.0089 (14) | −0.0286 (16) | −0.0139 (15) |
C24 | 0.0674 (16) | 0.0465 (15) | 0.082 (2) | 0.0116 (13) | −0.0253 (15) | −0.0088 (14) |
N1 | 0.0520 (11) | 0.0577 (13) | 0.0573 (16) | 0.0025 (11) | −0.0050 (10) | −0.0065 (11) |
N2 | 0.0664 (14) | 0.0566 (14) | 0.0792 (19) | 0.0067 (12) | −0.0090 (12) | −0.0127 (13) |
N3 | 0.0627 (13) | 0.0518 (13) | 0.0696 (17) | 0.0071 (11) | −0.0129 (12) | −0.0119 (12) |
N4 | 0.0520 (11) | 0.0410 (11) | 0.0625 (16) | 0.0040 (10) | −0.0124 (10) | −0.0044 (10) |
O1 | 0.0985 (15) | 0.0523 (12) | 0.1039 (19) | 0.0276 (11) | −0.0425 (13) | −0.0197 (12) |
O2 | 0.0611 (11) | 0.0579 (11) | 0.0842 (16) | 0.0031 (9) | −0.0205 (10) | −0.0145 (10) |
S1 | 0.0548 (4) | 0.0376 (3) | 0.0585 (5) | 0.0043 (3) | −0.0103 (3) | −0.0054 (3) |
C1—C2 | 1.525 (5) | C13—C16 | 1.504 (3) |
C1—H1A | 0.9600 | C14—C15 | 1.411 (3) |
C1—H1B | 0.9600 | C14—C17 | 1.465 (3) |
C1—H1C | 0.9600 | C15—N4 | 1.351 (3) |
C2—C7 | 1.363 (5) | C15—S1 | 1.717 (2) |
C2—C3 | 1.379 (5) | C16—H16A | 0.9600 |
C3—C4 | 1.392 (5) | C16—H16B | 0.9600 |
C3—H3 | 0.9300 | C16—H16C | 0.9600 |
C4—C5 | 1.376 (4) | C17—O2 | 1.238 (3) |
C4—H4 | 0.9300 | C17—C18 | 1.509 (3) |
C5—C6 | 1.374 (4) | C18—H18A | 0.9600 |
C5—N1 | 1.436 (3) | C18—H18B | 0.9600 |
C6—C7 | 1.385 (4) | C18—H18C | 0.9600 |
C6—H6 | 0.9300 | C19—C24 | 1.378 (3) |
C7—H7 | 0.9300 | C19—C20 | 1.383 (3) |
C8—C9 | 1.493 (3) | C19—N4 | 1.404 (3) |
C8—H8A | 0.9600 | C20—C21 | 1.381 (4) |
C8—H8B | 0.9600 | C20—H20 | 0.9300 |
C8—H8C | 0.9600 | C21—C22 | 1.368 (4) |
C9—N1 | 1.344 (3) | C21—H21 | 0.9300 |
C9—C10 | 1.377 (3) | C22—C23 | 1.362 (4) |
C10—N3 | 1.363 (3) | C22—H22 | 0.9300 |
C10—C11 | 1.473 (4) | C23—C24 | 1.382 (4) |
C11—O1 | 1.237 (3) | C23—H23 | 0.9300 |
C11—C12 | 1.458 (3) | C24—H24 | 0.9300 |
C12—C13 | 1.380 (3) | N1—N2 | 1.373 (3) |
C12—S1 | 1.748 (2) | N2—N3 | 1.302 (3) |
C13—C14 | 1.425 (3) | N4—H4A | 0.8600 |
C2—C1—H1A | 109.5 | C13—C14—C17 | 128.7 (2) |
C2—C1—H1B | 109.5 | N4—C15—C14 | 124.0 (2) |
H1A—C1—H1B | 109.5 | N4—C15—S1 | 123.54 (18) |
C2—C1—H1C | 109.5 | C14—C15—S1 | 112.40 (17) |
H1A—C1—H1C | 109.5 | C13—C16—H16A | 109.5 |
H1B—C1—H1C | 109.5 | C13—C16—H16B | 109.5 |
C7—C2—C3 | 118.1 (3) | H16A—C16—H16B | 109.5 |
C7—C2—C1 | 121.1 (5) | C13—C16—H16C | 109.5 |
C3—C2—C1 | 120.8 (4) | H16A—C16—H16C | 109.5 |
C2—C3—C4 | 121.8 (3) | H16B—C16—H16C | 109.5 |
C2—C3—H3 | 119.1 | O2—C17—C14 | 120.7 (2) |
C4—C3—H3 | 119.1 | O2—C17—C18 | 116.8 (2) |
C5—C4—C3 | 118.4 (4) | C14—C17—C18 | 122.5 (2) |
C5—C4—H4 | 120.8 | C17—C18—H18A | 109.5 |
C3—C4—H4 | 120.8 | C17—C18—H18B | 109.5 |
C6—C5—C4 | 120.6 (3) | H18A—C18—H18B | 109.5 |
C6—C5—N1 | 120.0 (3) | C17—C18—H18C | 109.5 |
C4—C5—N1 | 119.4 (3) | H18A—C18—H18C | 109.5 |
C5—C6—C7 | 119.4 (3) | H18B—C18—H18C | 109.5 |
C5—C6—H6 | 120.3 | C24—C19—C20 | 119.2 (2) |
C7—C6—H6 | 120.3 | C24—C19—N4 | 124.9 (2) |
C2—C7—C6 | 121.5 (4) | C20—C19—N4 | 115.9 (2) |
C2—C7—H7 | 119.2 | C21—C20—C19 | 119.7 (3) |
C6—C7—H7 | 119.2 | C21—C20—H20 | 120.1 |
C9—C8—H8A | 109.5 | C19—C20—H20 | 120.1 |
C9—C8—H8B | 109.5 | C22—C21—C20 | 121.0 (3) |
H8A—C8—H8B | 109.5 | C22—C21—H21 | 119.5 |
C9—C8—H8C | 109.5 | C20—C21—H21 | 119.5 |
H8A—C8—H8C | 109.5 | C23—C22—C21 | 119.0 (3) |
H8B—C8—H8C | 109.5 | C23—C22—H22 | 120.5 |
N1—C9—C10 | 104.1 (2) | C21—C22—H22 | 120.5 |
N1—C9—C8 | 123.7 (2) | C22—C23—C24 | 121.1 (3) |
C10—C9—C8 | 132.1 (2) | C22—C23—H23 | 119.4 |
N3—C10—C9 | 108.9 (2) | C24—C23—H23 | 119.4 |
N3—C10—C11 | 124.3 (2) | C19—C24—C23 | 119.9 (2) |
C9—C10—C11 | 126.8 (2) | C19—C24—H24 | 120.1 |
O1—C11—C12 | 121.1 (2) | C23—C24—H24 | 120.1 |
O1—C11—C10 | 116.2 (2) | C9—N1—N2 | 111.1 (2) |
C12—C11—C10 | 122.7 (2) | C9—N1—C5 | 129.3 (2) |
C13—C12—C11 | 127.6 (2) | N2—N1—C5 | 119.6 (2) |
C13—C12—S1 | 111.51 (17) | N3—N2—N1 | 106.6 (2) |
C11—C12—S1 | 120.89 (19) | N2—N3—C10 | 109.4 (2) |
C12—C13—C14 | 113.3 (2) | C15—N4—C19 | 132.0 (2) |
C12—C13—C16 | 122.1 (2) | C15—N4—H4A | 114.0 |
C14—C13—C16 | 124.6 (2) | C19—N4—H4A | 114.0 |
C15—C14—C13 | 111.2 (2) | C15—S1—C12 | 91.53 (11) |
C15—C14—C17 | 120.0 (2) |
Funding information
The project was supported by King Saud University, Deanship of Scientific Research, Research Chairs and Cardiff University.
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