research communications
N-[(Z)-4-propoxybenzylidene]-1,3-thiazol-2-amine
and Hirshfeld surface analysis of 4-(naphthalen-2-yl)-aSalahaddin University, College of Science, Department of Chemistry, Erbil, Iraq, bKoya University, Faculty of Science and Health, Department of Chemistry, Koya, Iraq, and cSalahaddin University, College of Education, Department of Chemistry, Erbil, Iraq
*Correspondence e-mail: ropak.shekhmohamad@su.edu.krd, wali.hmd@koyauniversity.org
The 23H20N2OS, contains one slightly bent molecule. The naphthalene ring system and the thiazole ring are twisted with respect to each other, making a dihedral angle of 13.69 (10)°; the anisole ring is inclined to the plane of the naphthalene ring system, the dihedral angle being 14.22 (12)°. In the molecules are linked by C—H⋯π interactions, resulting in the formation of sheets parallel to (100). Within the sheets, very weak π–π stacking interactions lead to additional stabilization. Hirshfeld surface analysis and fingerprint plots reveal that the cohesion in the is dominated by H⋯H (42.5%) and C⋯H/H⋯C (37.2%) contacts.
of the title compound, CKeywords: Crystal structure; heterocyclic compound; thiazole; Schiff base; Hirshfeld surface analysis; crystal structure.
CCDC reference: 2004309
1. Chemical context
A Schiff base (Schiff, 1864) is a compound having the general formula RN=CR2 (R = H, hydrocarbyl) and thus belongs to the family of (McNaught & Wilkinson, 1997). The chemistry of and their derivatives has been an interesting field of research since their discovery. Subsequently, have constituted a significant class of compounds for new drug development, exhibiting biological activities including antimicrobial, anti-tuberculosis, antioxidant, anti-inflammatory, anticonvulsant, antidepressant, anxiolytic, antihypertensive, anticancer and antifungal properties. The search for Schiff base-containing compounds with more selective activity and lower side effects continues to be an active area in medicinal chemistry (Kumar et al., 2017). Likewise, play an essential role in medicinal chemistry, or as key templates for the development of various therapeutic agents. As part of this family, thiazoles (Ghawla Amit et al., 2014) and their derivatives have been found to possess anticonvulsant, antimicrobial, anti-inflammatory, anticancer, anti-HIV, antidiabetic, anti-Alzheimer, antihypertensive, and antioxidant activities. As a result of their potent and significant biological activities, they have excellent pharmaceutical importance (Kaur & Goyal, 2018).
Here we report on the synthesis, 23H20N2OS, (I), comprising a thiazole entity.
and Hirshfeld analysis of a Schiff base, C2. Structural commentary
The I) contains one molecule (Fig. 1). The molecule is slightly bent, with the naphthalene ring system and the thiazole ring inclined to each other, subtending a dihedral angle of 13.69 (10)°; the anisole moiety is inclined to the plane of the naphthalene ring system, the dihedral angle being 14.22 (12)°. The C18—O1 and C21—O1 bond lengths are typical of single bonds (Table 1). The bond-length distribution in the thiazole ring is normal. The C11—N1 bond has single-bond character and the C13—N1 bond double-bond character, with bond lengths of 1.380 (3) and 1.304 (3) Å, respectively.
of (
|
3. Supramolecular features
In the Cg3i and C16—H16⋯Cg3ii interactions (Table 2; Fig. 2), where Cg3 is the centroid of the C5–C10 ring. Within the sheets, very weak π–π stacking interactions are observed with a centroid-to-centroid distance Cg1⋯Cg4 = 4.494 (2) Å, where Cg1 and Cg4 are the centroids of the S1/C12/C11/N1/C13 and the C15–C20 phenyl ring, respectively (Fig. 3).
molecules are connected into sheets extending along (100) by C4—H4⋯4. Database survey
A search of the Cambridge Structural Database (CSD, version 5.40, update November 2018; Groom et al., 2016) for the 4-(4,6-dihydronaphthalen-1-yl)thiazol-2-amine moiety revealed two hits, viz. 4-(pyren-1-yl)-1,3-thiazol-2-amine (pyrene thiazole conjugate, PTC), C19H12N2S (SOPREW; Mahapatra et al., 2014), and (E)-4-(4-chlorophenyl)-N-(1,3-benzodioxol-5-ylmethylene)-5-(1H-1,2,4-triazol-1-yl)-1,3-thiazol-2-amine, C19H12ClN5O2S (XAZJUE; Shao et al., 2006). In the crystal packing of PTC, the two molecules are connected into symmetrical dimers by pairs of N—H⋯N hydrogen bonds at a distance of 2.49 Å and are stacked along the a axis by weak aromatic π–π stacking interactions between the benzene rings in adjacent molecules [centroid-to-centroid distances of 3.5741 (10) Å]. Distinctive bond lengths (e.g. N1—C11, N—C13, S1—C12, S1—C13) in (I) are the same within standard deviations as the corresponding bond lengths in the structure of XAZJUE. In XAZJUE, the molecules are linked by weak C—H⋯O hydrogen bonds into a three-dimensional network.
5. Hirshfeld surface analysis
Hirshfeld surface analysis (Spackman & Jayatilaka, 2009; McKinnon et al., 2007) was carried out using CrystalExplorer17.5 (Turner et al., 2017). The Hirshfeld surface and their associated two-dimensional fingerprint plots were used to quantify the various intermolecular interactions in (I). Hirshfeld surface analysis was performed using a standard (high) surface resolution with the three-dimensional dnorm surfaces mapped over a fixed colour scale of −0.0638 (red) to 1.3242 (blue) a.u., and the results are illustrated in Fig. 4a. The red spots identified in Fig. 4a correspond to the near-type H⋯π contacts resulting from hydrogen bonds of the type C—H⋯π(ring) (Table 2). The view of the three-dimensional Hirshfeld surface of the title compound plotted over electrostatic potentials with a fixed colour scale of −0.049 (red) to 0.034 (blue) a.u. is given in Fig. 4b, emphasizing on C—H⋯π(ring) contacts.
Fig. 5a shows the two-dimensional fingerprint as the sum of all contacts contributing to the Hirshfeld surface indicated in normal mode. Fig. 5b illustrates the two-dimensional fingerprint of (di, de) points related to H⋯H contacts that represent a 42.5% contribution in the title structure. In Fig. 5c, two symmetrical wings on the left and right sides indicate C⋯H/H⋯C interactions with a contribution of 37.2%. Furthermore, there are S⋯H/H⋯S (8.2%; Fig. 5d), N⋯H/H⋯N (7.5%; Fig. 5e) and O⋯H/H⋯O (2.2%; Fig. 5f) contacts contributing to the overall crystal packing of (I).
6. Synthesis and crystallization
Compound (I) was prepared by adding 4-N-propoxybenzaldehyde (0.145 g, 0.885 mmol) dropwise under constant stirring to a solution of 2-amino-4-(2-naphthyl)thiazole (0.2 g, 0.885 mmol) in 1-propanol (10 ml). The reaction was catalysed by NaOH (0.1 g), and the mixture stirred for 1 h in a water bath at approximately 278–283 K. The reaction was monitored by (TLC) using ethyl acetate and n-hexane (3:7 v:v), and had an Rf of 0.675. The formed precipitate was filtered off, washed with 1-propanol, and dried. The resulting solid was further purified by washing with ethanol and diethyl ether. Single crystals of (I) for X-ray analysis were obtained by slow evaporation of an acetone solution (yield 60%, m.p. 411-413 K).
7. Refinement
Crystal data, data collection and structure . The C-bound H atoms were placed in idealized positions and refined using a riding model with C—H = 0.93-0.97 Å and Uiso(H) = 1.5Ueq(C-methyl) or 1.2Ueq(C) for other C-bound H atoms.
details are summarized in Table 3Supporting information
CCDC reference: 2004309
https://doi.org/10.1107/S2056989020006611/wm5556sup1.cif
contains datablock I. DOI:Structure factors: contains datablock I. DOI: https://doi.org/10.1107/S2056989020006611/wm5556Isup2.hkl
Supporting information file. DOI: https://doi.org/10.1107/S2056989020006611/wm5556Isup3.cml
Data collection: X-AREA (Stoe & Cie, 2002); cell
X-AREA (Stoe & Cie, 2002); data reduction: X-RED (Stoe & Cie, 2002); program(s) used to solve structure: SHELXT2017/1 (Sheldrick, 2015a); program(s) used to refine structure: SHELXL2017/1 (Sheldrick, 2015b); molecular graphics: PLATON (Spek, 2020); software used to prepare material for publication: WinGX (Farrugia, 2012).C23H20N2OS | F(000) = 784 |
Mr = 372.47 | Dx = 1.294 Mg m−3 |
Monoclinic, P21/c | Mo Kα radiation, λ = 0.71073 Å |
a = 19.1636 (11) Å | Cell parameters from 9076 reflections |
b = 6.0482 (3) Å | θ = 1.8–31.6° |
c = 17.023 (1) Å | µ = 0.18 mm−1 |
β = 104.370 (5)° | T = 296 K |
V = 1911.32 (19) Å3 | Stick, yellow |
Z = 4 | 0.68 × 0.29 × 0.05 mm |
STOE IPDS 2 diffractometer | 3770 independent reflections |
Radiation source: sealed X-ray tube, 12 x 0.4 mm long-fine focus | 1951 reflections with I > 2σ(I) |
Detector resolution: 6.67 pixels mm-1 | Rint = 0.078 |
rotation method scans | θmax = 26.0°, θmin = 2.2° |
Absorption correction: integration (X-RED32; Stoe & Cie, 2002) | h = −19→23 |
Tmin = 0.919, Tmax = 0.989 | k = −7→7 |
12341 measured reflections | l = −20→20 |
Refinement on F2 | 0 restraints |
Least-squares matrix: full | Hydrogen site location: inferred from neighbouring sites |
R[F2 > 2σ(F2)] = 0.056 | H-atom parameters constrained |
wR(F2) = 0.087 | w = 1/[σ2(Fo2) + (0.0235P)2] where P = (Fo2 + 2Fc2)/3 |
S = 0.96 | (Δ/σ)max < 0.001 |
3770 reflections | Δρmax = 0.12 e Å−3 |
245 parameters | Δρmin = −0.16 e Å−3 |
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 | ||
S1 | 0.72771 (5) | 0.01821 (13) | 0.45111 (4) | 0.0700 (2) | |
O1 | 0.57359 (10) | 0.7728 (3) | −0.00225 (10) | 0.0614 (5) | |
N1 | 0.78855 (12) | 0.3982 (3) | 0.46984 (12) | 0.0518 (6) | |
N2 | 0.71496 (12) | 0.3175 (4) | 0.33523 (12) | 0.0574 (6) | |
C15 | 0.69256 (14) | 0.5693 (4) | 0.22324 (14) | 0.0471 (6) | |
C6 | 0.88892 (13) | 0.4646 (4) | 0.76167 (14) | 0.0486 (6) | |
C8 | 0.84752 (13) | 0.4163 (4) | 0.61580 (15) | 0.0467 (6) | |
C11 | 0.80536 (13) | 0.2954 (4) | 0.54458 (15) | 0.0481 (6) | |
C7 | 0.85390 (13) | 0.3407 (4) | 0.69324 (15) | 0.0497 (7) | |
H7 | 0.834523 | 0.203683 | 0.700743 | 0.060* | |
C20 | 0.63762 (14) | 0.4417 (4) | 0.17593 (14) | 0.0552 (7) | |
H20 | 0.626787 | 0.304989 | 0.194986 | 0.066* | |
C18 | 0.61554 (13) | 0.7170 (4) | 0.07205 (14) | 0.0494 (7) | |
C13 | 0.74782 (15) | 0.2697 (4) | 0.41597 (15) | 0.0526 (7) | |
C5 | 0.91907 (14) | 0.6724 (4) | 0.75068 (16) | 0.0520 (7) | |
C9 | 0.87997 (14) | 0.6206 (4) | 0.60570 (16) | 0.0542 (7) | |
H9 | 0.877676 | 0.671926 | 0.553618 | 0.065* | |
C19 | 0.59913 (14) | 0.5150 (5) | 0.10142 (14) | 0.0557 (7) | |
H19 | 0.562053 | 0.428985 | 0.070646 | 0.067* | |
C10 | 0.91444 (14) | 0.7434 (5) | 0.67047 (16) | 0.0581 (7) | |
H10 | 0.935420 | 0.876963 | 0.661879 | 0.070* | |
C17 | 0.67016 (15) | 0.8446 (5) | 0.11727 (16) | 0.0570 (7) | |
H17 | 0.681829 | 0.979223 | 0.097421 | 0.068* | |
C14 | 0.72982 (13) | 0.5003 (5) | 0.30469 (13) | 0.0548 (7) | |
H14 | 0.765398 | 0.591233 | 0.335507 | 0.066* | |
C16 | 0.70766 (14) | 0.7699 (5) | 0.19294 (15) | 0.0574 (7) | |
H16 | 0.744007 | 0.857655 | 0.224102 | 0.069* | |
C1 | 0.89269 (14) | 0.3919 (5) | 0.84200 (16) | 0.0592 (7) | |
H1 | 0.873907 | 0.254632 | 0.850405 | 0.071* | |
C12 | 0.77718 (16) | 0.0891 (4) | 0.54435 (16) | 0.0617 (7) | |
H12 | 0.784240 | −0.001549 | 0.589769 | 0.074* | |
C2 | 0.92348 (16) | 0.5211 (6) | 0.90667 (17) | 0.0732 (9) | |
H2 | 0.924833 | 0.472661 | 0.958877 | 0.088* | |
C21 | 0.59299 (17) | 0.9645 (5) | −0.04130 (15) | 0.0699 (8) | |
H21A | 0.642670 | 0.953582 | −0.044645 | 0.084* | |
H21B | 0.587991 | 1.096221 | −0.010673 | 0.084* | |
C4 | 0.95124 (16) | 0.7990 (5) | 0.81968 (18) | 0.0696 (8) | |
H4 | 0.971585 | 0.935292 | 0.813145 | 0.084* | |
C3 | 0.95304 (17) | 0.7257 (6) | 0.89530 (18) | 0.0761 (9) | |
H3 | 0.974148 | 0.812465 | 0.939997 | 0.091* | |
C22 | 0.54367 (17) | 0.9770 (6) | −0.12479 (17) | 0.0846 (10) | |
H22A | 0.554784 | 1.109652 | −0.151339 | 0.102* | |
H22B | 0.494394 | 0.989504 | −0.120138 | 0.102* | |
C23 | 0.54931 (19) | 0.7806 (7) | −0.17675 (18) | 0.0990 (12) | |
H23A | 0.518100 | 0.801144 | −0.229840 | 0.149* | |
H23B | 0.535317 | 0.649628 | −0.152709 | 0.149* | |
H23C | 0.598123 | 0.765472 | −0.180940 | 0.149* |
U11 | U22 | U33 | U12 | U13 | U23 | |
S1 | 0.0868 (6) | 0.0596 (5) | 0.0589 (4) | −0.0121 (5) | 0.0092 (4) | 0.0028 (4) |
O1 | 0.0618 (12) | 0.0702 (13) | 0.0472 (10) | −0.0091 (10) | 0.0041 (9) | 0.0089 (9) |
N1 | 0.0573 (14) | 0.0520 (13) | 0.0459 (13) | 0.0032 (12) | 0.0128 (11) | 0.0038 (11) |
N2 | 0.0621 (15) | 0.0622 (15) | 0.0476 (13) | 0.0043 (13) | 0.0130 (11) | 0.0051 (12) |
C15 | 0.0488 (16) | 0.0527 (17) | 0.0402 (13) | −0.0014 (14) | 0.0117 (12) | −0.0031 (12) |
C6 | 0.0387 (14) | 0.0577 (17) | 0.0493 (14) | 0.0052 (14) | 0.0107 (12) | 0.0021 (14) |
C8 | 0.0437 (15) | 0.0471 (15) | 0.0496 (16) | 0.0062 (13) | 0.0123 (12) | 0.0080 (12) |
C11 | 0.0460 (15) | 0.0497 (16) | 0.0494 (15) | 0.0075 (13) | 0.0134 (13) | 0.0084 (13) |
C7 | 0.0462 (16) | 0.0480 (16) | 0.0553 (16) | −0.0014 (13) | 0.0136 (13) | 0.0053 (13) |
C20 | 0.0679 (19) | 0.0524 (17) | 0.0463 (15) | −0.0097 (15) | 0.0159 (14) | 0.0010 (13) |
C18 | 0.0457 (15) | 0.0578 (18) | 0.0437 (15) | −0.0019 (14) | 0.0093 (12) | −0.0005 (13) |
C13 | 0.0562 (17) | 0.0571 (18) | 0.0452 (15) | 0.0088 (15) | 0.0140 (13) | 0.0041 (14) |
C5 | 0.0432 (16) | 0.0509 (17) | 0.0607 (18) | 0.0018 (14) | 0.0103 (13) | 0.0005 (14) |
C9 | 0.0556 (17) | 0.0562 (17) | 0.0497 (16) | 0.0031 (15) | 0.0107 (14) | 0.0123 (13) |
C19 | 0.0610 (17) | 0.0587 (18) | 0.0450 (14) | −0.0186 (16) | 0.0085 (13) | −0.0065 (14) |
C10 | 0.0540 (17) | 0.0513 (17) | 0.0680 (19) | 0.0011 (15) | 0.0135 (15) | 0.0109 (15) |
C17 | 0.0616 (18) | 0.0525 (17) | 0.0563 (17) | −0.0101 (15) | 0.0135 (14) | 0.0033 (13) |
C14 | 0.0522 (17) | 0.0664 (19) | 0.0446 (14) | 0.0054 (16) | 0.0101 (12) | −0.0054 (15) |
C16 | 0.0545 (17) | 0.0619 (19) | 0.0534 (17) | −0.0124 (15) | 0.0085 (14) | −0.0033 (14) |
C1 | 0.0509 (17) | 0.073 (2) | 0.0528 (17) | −0.0034 (15) | 0.0119 (14) | 0.0007 (15) |
C12 | 0.0750 (19) | 0.0530 (18) | 0.0530 (16) | −0.0017 (17) | 0.0079 (14) | 0.0076 (14) |
C2 | 0.072 (2) | 0.094 (2) | 0.0542 (17) | −0.005 (2) | 0.0168 (15) | −0.0041 (18) |
C21 | 0.085 (2) | 0.0626 (19) | 0.0587 (17) | −0.0039 (18) | 0.0113 (16) | 0.0097 (16) |
C4 | 0.066 (2) | 0.067 (2) | 0.075 (2) | −0.0083 (17) | 0.0159 (17) | −0.0091 (17) |
C3 | 0.076 (2) | 0.087 (3) | 0.062 (2) | −0.012 (2) | 0.0097 (17) | −0.0188 (18) |
C22 | 0.084 (2) | 0.099 (3) | 0.0621 (19) | −0.002 (2) | 0.0013 (17) | 0.028 (2) |
C23 | 0.100 (3) | 0.139 (3) | 0.0546 (19) | −0.035 (3) | 0.0144 (19) | −0.005 (2) |
S1—C12 | 1.690 (3) | C9—C10 | 1.357 (4) |
S1—C13 | 1.713 (3) | C9—H9 | 0.9300 |
O1—C18 | 1.362 (3) | C19—H19 | 0.9300 |
O1—C21 | 1.431 (3) | C10—H10 | 0.9300 |
N1—C13 | 1.304 (3) | C17—C16 | 1.386 (3) |
N1—C11 | 1.380 (3) | C17—H17 | 0.9300 |
N2—C14 | 1.284 (3) | C14—H14 | 0.9300 |
N2—C13 | 1.393 (3) | C16—H16 | 0.9300 |
C15—C16 | 1.377 (3) | C1—C2 | 1.360 (4) |
C15—C20 | 1.390 (3) | C1—H1 | 0.9300 |
C15—C14 | 1.454 (3) | C12—H12 | 0.9300 |
C6—C7 | 1.407 (3) | C2—C3 | 1.394 (4) |
C6—C5 | 1.415 (3) | C2—H2 | 0.9300 |
C6—C1 | 1.421 (3) | C21—C22 | 1.501 (3) |
C8—C7 | 1.372 (3) | C21—H21A | 0.9700 |
C8—C9 | 1.413 (3) | C21—H21B | 0.9700 |
C8—C11 | 1.473 (3) | C4—C3 | 1.354 (4) |
C11—C12 | 1.359 (3) | C4—H4 | 0.9300 |
C7—H7 | 0.9300 | C3—H3 | 0.9300 |
C20—C19 | 1.373 (3) | C22—C23 | 1.501 (4) |
C20—H20 | 0.9300 | C22—H22A | 0.9700 |
C18—C17 | 1.372 (3) | C22—H22B | 0.9700 |
C18—C19 | 1.386 (3) | C23—H23A | 0.9600 |
C5—C4 | 1.409 (4) | C23—H23B | 0.9600 |
C5—C10 | 1.413 (3) | C23—H23C | 0.9600 |
C12—S1—C13 | 88.87 (14) | C18—C17—H17 | 120.5 |
C18—O1—C21 | 118.1 (2) | C16—C17—H17 | 120.5 |
C13—N1—C11 | 110.0 (2) | N2—C14—C15 | 121.8 (3) |
C14—N2—C13 | 119.1 (2) | N2—C14—H14 | 119.1 |
C16—C15—C20 | 118.1 (2) | C15—C14—H14 | 119.1 |
C16—C15—C14 | 120.7 (3) | C15—C16—C17 | 121.8 (3) |
C20—C15—C14 | 121.0 (2) | C15—C16—H16 | 119.1 |
C7—C6—C5 | 119.3 (2) | C17—C16—H16 | 119.1 |
C7—C6—C1 | 122.1 (3) | C2—C1—C6 | 120.6 (3) |
C5—C6—C1 | 118.5 (2) | C2—C1—H1 | 119.7 |
C7—C8—C9 | 118.1 (2) | C6—C1—H1 | 119.7 |
C7—C8—C11 | 121.7 (2) | C11—C12—S1 | 111.4 (2) |
C9—C8—C11 | 120.1 (2) | C11—C12—H12 | 124.3 |
C12—C11—N1 | 114.2 (2) | S1—C12—H12 | 124.3 |
C12—C11—C8 | 126.4 (2) | C1—C2—C3 | 120.5 (3) |
N1—C11—C8 | 119.3 (2) | C1—C2—H2 | 119.8 |
C8—C7—C6 | 121.9 (2) | C3—C2—H2 | 119.8 |
C8—C7—H7 | 119.0 | O1—C21—C22 | 107.8 (2) |
C6—C7—H7 | 119.0 | O1—C21—H21A | 110.1 |
C19—C20—C15 | 120.8 (2) | C22—C21—H21A | 110.1 |
C19—C20—H20 | 119.6 | O1—C21—H21B | 110.1 |
C15—C20—H20 | 119.6 | C22—C21—H21B | 110.1 |
O1—C18—C17 | 125.0 (2) | H21A—C21—H21B | 108.5 |
O1—C18—C19 | 114.8 (2) | C3—C4—C5 | 121.1 (3) |
C17—C18—C19 | 120.2 (2) | C3—C4—H4 | 119.4 |
N1—C13—N2 | 128.0 (2) | C5—C4—H4 | 119.4 |
N1—C13—S1 | 115.54 (19) | C4—C3—C2 | 120.5 (3) |
N2—C13—S1 | 116.3 (2) | C4—C3—H3 | 119.8 |
C4—C5—C10 | 123.4 (3) | C2—C3—H3 | 119.8 |
C4—C5—C6 | 118.8 (2) | C21—C22—C23 | 113.4 (3) |
C10—C5—C6 | 117.9 (2) | C21—C22—H22A | 108.9 |
C10—C9—C8 | 121.3 (2) | C23—C22—H22A | 108.9 |
C10—C9—H9 | 119.3 | C21—C22—H22B | 108.9 |
C8—C9—H9 | 119.3 | C23—C22—H22B | 108.9 |
C20—C19—C18 | 120.0 (2) | H22A—C22—H22B | 107.7 |
C20—C19—H19 | 120.0 | C22—C23—H23A | 109.5 |
C18—C19—H19 | 120.0 | C22—C23—H23B | 109.5 |
C9—C10—C5 | 121.3 (3) | H23A—C23—H23B | 109.5 |
C9—C10—H10 | 119.3 | C22—C23—H23C | 109.5 |
C5—C10—H10 | 119.3 | H23A—C23—H23C | 109.5 |
C18—C17—C16 | 119.0 (2) | H23B—C23—H23C | 109.5 |
C13—N1—C11—C12 | 0.8 (3) | C15—C20—C19—C18 | 0.9 (4) |
C13—N1—C11—C8 | −176.4 (2) | O1—C18—C19—C20 | −179.7 (2) |
C7—C8—C11—C12 | −9.7 (4) | C17—C18—C19—C20 | −0.1 (4) |
C9—C8—C11—C12 | 173.2 (3) | C8—C9—C10—C5 | −0.2 (4) |
C7—C8—C11—N1 | 167.1 (2) | C4—C5—C10—C9 | −176.9 (3) |
C9—C8—C11—N1 | −10.0 (3) | C6—C5—C10—C9 | 2.3 (4) |
C9—C8—C7—C6 | 2.6 (4) | O1—C18—C17—C16 | 178.6 (2) |
C11—C8—C7—C6 | −174.5 (2) | C19—C18—C17—C16 | −1.0 (4) |
C5—C6—C7—C8 | −0.5 (4) | C13—N2—C14—C15 | −174.3 (2) |
C1—C6—C7—C8 | 176.9 (2) | C16—C15—C14—N2 | 177.6 (3) |
C16—C15—C20—C19 | −0.6 (4) | C20—C15—C14—N2 | 1.9 (4) |
C14—C15—C20—C19 | 175.3 (2) | C20—C15—C16—C17 | −0.5 (4) |
C21—O1—C18—C17 | 8.3 (4) | C14—C15—C16—C17 | −176.4 (2) |
C21—O1—C18—C19 | −172.1 (2) | C18—C17—C16—C15 | 1.3 (4) |
C11—N1—C13—N2 | 174.8 (2) | C7—C6—C1—C2 | −176.4 (3) |
C11—N1—C13—S1 | −0.4 (3) | C5—C6—C1—C2 | 1.1 (4) |
C14—N2—C13—N1 | 7.1 (4) | N1—C11—C12—S1 | −0.9 (3) |
C14—N2—C13—S1 | −177.7 (2) | C8—C11—C12—S1 | 176.1 (2) |
C12—S1—C13—N1 | 0.0 (2) | C13—S1—C12—C11 | 0.5 (2) |
C12—S1—C13—N2 | −175.9 (2) | C6—C1—C2—C3 | −1.1 (4) |
C7—C6—C5—C4 | 177.3 (2) | C18—O1—C21—C22 | 174.3 (2) |
C1—C6—C5—C4 | −0.3 (4) | C10—C5—C4—C3 | 178.6 (3) |
C7—C6—C5—C10 | −1.9 (4) | C6—C5—C4—C3 | −0.5 (4) |
C1—C6—C5—C10 | −179.5 (2) | C5—C4—C3—C2 | 0.6 (5) |
C7—C8—C9—C10 | −2.3 (4) | C1—C2—C3—C4 | 0.3 (5) |
C11—C8—C9—C10 | 174.9 (2) | O1—C21—C22—C23 | −61.0 (3) |
Cg3 is the centroid of the C5–C10 ring. |
D—H···A | D—H | H···A | D···A | D—H···A |
C4—H4···Cg3i | 0.93 | 2.83 | 3.496 | 130 |
C16—H16···Cg3ii | 0.93 | 3.00 | 3.607 | 125 |
Symmetry codes: (i) −x, y+1/2, −z−1/2; (ii) x, −y+1/2, z+1/2. |
Acknowledgements
This study was supported by Ondokuz Mayıs University under project No. PYO·FEN.1906.19.001.
Funding information
Funding for this research was provided by: Ondokuz Mayıs University (award No. PYO.FEN.1906.19.001).
References
Farrugia, L. J. (2012). J. Appl. Cryst. 45, 849–854. Web of Science CrossRef CAS IUCr Journals Google Scholar
Ghawla Amit, C. P., Sunaina, Singh Mansimran, Kaur Kuldeep & Dhawan, R. K. (2014). Int. J. Pharmacol. Pharm. Sci. 2, 1–8. Google Scholar
Groom, C. R., Bruno, I. J., Lightfoot, M. P. & Ward, S. C. (2016). Acta Cryst. B72, 171–179. Web of Science CrossRef IUCr Journals Google Scholar
Kaur, H. & Goyal, A. (2018). Int. J. Pharm. Drug. Anal, 6, 509–522. Google Scholar
Kumar, J., Rai, A. & Raj, V. (2017). Org. Med. Chem. J. 1, 555–564. Google Scholar
Mahapatra, A. K., Mondal, S., Maiti, K., Manna, S. K., Maji, R., Mandal, D., Mandal, S., Goswami, S., Quah, C. K. & Fun, H.-K. (2014). RSC Adv. 4, 56605–56614. Google Scholar
McKinnon, J. J., Jayatilaka, D. & Spackman, M. A. (2007). Chem. Commun. pp. 3814–3816. Web of Science CrossRef Google Scholar
McNaught, A. D. & Wilkinson, A. (1997). Compendium of Chemical Terminology. Blackwell Science Oxford. Google Scholar
Schiff, H. (1864). Ann. Chem. Pharm. 131, 118–119. CrossRef Google Scholar
Shao, L., Zhang, Q., Zhou, X. & Fang, J.-X. (2006). Acta Cryst. E62, o334–o335. 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
Spackman, M. A. & Jayatilaka, D. (2009). CrystEngComm, 11, 19–32. Web of Science CrossRef CAS Google Scholar
Spek, A. L. (2020). Acta Cryst. E76, 1–11. Web of Science CrossRef IUCr Journals Google Scholar
Stoe & Cie (2002). X-AREA and X-RED32. Stoe & Cie GmbH, Darmstadt, Germany. Google Scholar
Turner, M. J., MacKinnon, J. J., Wolff, S. K., Grimwood, D. J., Spackman, P. R., Jayatilaka, D. & Spackman, M. A. (2017). Crystal Explorer 17.5. University of Western Australia. https://hirshfeldsurface.net. Google Scholar
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