organic compounds
3-{2-[3-(4-Chlorophenyl)-5-(4-fluorophenyl)-4,5-dihydro-1H-pyrazol-1-yl]thiazol-4-yl}-3,8a-dihydro-2H-chromen-2-one
aDepartment 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, dPharmaceutical Chemistry Department, College of Pharmacy, Umm Al-Qura University, Makkah, Saudi Arabia, and eSchool of Chemistry, Cardiff University, Main Building, Park Place, Cardiff CF10 3AT, UK
*Correspondence e-mail: gelhiti@ksu.edu.sa
The title compound, C27H17ClFN3O2S, comprises chromonyl (A), thiazolyl (B), pyrazolyl (C), chlorophenyl (D) and fluorophenyl (E) rings with twist angles between the planes of adjacent rings pairs A/B, B/C, C/D and C/E of 14.1 (1), 18.2 (2), 1.3 (1) and 4.9 (1)°, respectively. The is characterized by a range of intermolecular interactions including C—H⋯F, C—H⋯Cl and C—H⋯O contacts. Aromatic π–π stacking between chromonyl groups and chlorophenyl groups [centroid–centroid separations = 3.7170 (16) and 4.017 (2) Å, respectively] lead to columns of molecules propagating parallel to the [100] direction.
Keywords: crystal structure; chromen-2-one; pyrazole.
CCDC reference: 1894531
Structure description
). Thiazoles are an essential core scaffold in many natural products (Chhabria et al., 2016) and pyrazoles have a broad spectrum of biological activities (Faria et al., 2017). We now describe the synthesis and structure of the title compound.
act as anticoagulant drugs (O'Reilly & Aggeler, 1968The A), thiazolyl (B), pyrazolyl (C), chlorophenyl (D) and fluorophenyl (E) rings (Fig. 1). The twist angles between the planes through neighbouring rings pairs A/B, B/C, C/D and C/E are 14.1 (1), 18.2 (2), 1.3 (1) and 4.9 (1)°, respectively. The stereogenic centre C13 has an S configuration in the arbitrarily chosen but the crystal symmetry generates a racemic mixture.
consists of one molecule, which comprises chromonyl (The extended structure is characterized by a range of intermolecular interactions including C—H⋯F, C—H⋯Cl and C—H⋯O contacts (Table 1, Fig. 2). Aromatic π–π stacking between chromonyl groups [with centroid-to-centroid distances of 3.7170 (16) Å] and between chlorophenyl groups [with ring-centroid separations of 4.017 (2) Å] lead to the formation of columns propagating in the [100] direction (Fig. 3).
Synthesis and crystallization
The title compound was synthesized from the condensation of 3-(4-chlorophenyl)-5-(4-fluorophenyl)-4,5-dihydro-1H-pyrazole-1-carbothioamide (0.67 g, 2.0 mmol) with 3-(2-bromoacetyl)-3,8a-dihydro-2H-chromen-2-one (0.54 g, 2.0 mmol) in anhydrous ethanol (20 ml) under reflux for 2 h. The formed solid was recrystallized from dimethylformamide solution to give colourless blocks (83%), m.p. 228–230°C.
Refinement
Crystal data, data collection and structure .
details are summarized in Table 2Structural data
CCDC reference: 1894531
https://doi.org/10.1107/S2414314619001706/hb4283sup1.cif
contains datablock I. DOI:Structure factors: contains datablock I. DOI: https://doi.org/10.1107/S2414314619001706/hb4283Isup2.hkl
Supporting information file. DOI: https://doi.org/10.1107/S2414314619001706/hb4283Isup3.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: SHELXS (Sheldrick, 2008); program(s) used to refine structure: SHELXL2018 (Sheldrick, 2015); molecular graphics: ORTEP-3 for Windows and WinGX (Farrugia, 2012); software used to prepare material for publication: CHEMDRAW Ultra (Cambridge Soft, 2001).C27H17ClFN3O2S | Dx = 1.424 Mg m−3 |
Mr = 501.95 | Mo Kα radiation, λ = 0.71073 Å |
Orthorhombic, Pbca | Cell parameters from 3797 reflections |
a = 7.9243 (5) Å | θ = 4.0–25.8° |
b = 23.7112 (9) Å | µ = 0.29 mm−1 |
c = 24.9270 (15) Å | T = 296 K |
V = 4683.7 (4) Å3 | Block, colourless |
Z = 8 | 0.31 × 0.18 × 0.14 mm |
F(000) = 2064 |
Rigaku Oxford Diffraction SuperNova, Dual, Cu at zero, Atlas diffractometer | 3055 reflections with I > 2σ(I) |
ω scans | Rint = 0.044 |
Absorption correction: gaussian (CrysAlisPro; Rigaku OD, 2015) | θmax = 29.9°, θmin = 3.4° |
Tmin = 0.997, Tmax = 0.998 | h = −10→11 |
21351 measured reflections | k = −32→24 |
5809 independent reflections | l = −28→31 |
Refinement on F2 | Hydrogen site location: inferred from neighbouring sites |
Least-squares matrix: full | H-atom parameters constrained |
R[F2 > 2σ(F2)] = 0.058 | w = 1/[σ2(Fo2) + (0.0699P)2 + 1.7487P] where P = (Fo2 + 2Fc2)/3 |
wR(F2) = 0.184 | (Δ/σ)max = 0.001 |
S = 1.04 | Δρmax = 0.64 e Å−3 |
5809 reflections | Δρmin = −0.58 e Å−3 |
317 parameters | Extinction correction: SHELXL-2018/1 (Sheldrick 2018), Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4 |
0 restraints | Extinction coefficient: 0.0020 (4) |
Primary atom site location: structure-invariant direct methods |
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. Bond distances for sp2 C—H hydrogen atoms were set to 0.93 Å and their Uiso set to 1.2 times Ueq(C). Bond distances for methine and methylene C—H hydrogen atoms were set to 0.98 Å and 0.97 Å respectively and their Uiso set to 1.2 times Ueq(C). |
x | y | z | Uiso*/Ueq | ||
C1 | 0.6165 (5) | 0.40241 (12) | 0.44274 (13) | 0.0673 (9) | |
C2 | 0.6420 (3) | 0.38786 (11) | 0.49852 (12) | 0.0527 (7) | |
C3 | 0.7055 (4) | 0.42696 (11) | 0.53236 (13) | 0.0599 (8) | |
H3 | 0.723831 | 0.417008 | 0.567977 | 0.072* | |
C4 | 0.7455 (4) | 0.48295 (11) | 0.51563 (13) | 0.0606 (8) | |
C5 | 0.7184 (4) | 0.49645 (12) | 0.46241 (13) | 0.0630 (8) | |
C6 | 0.8068 (5) | 0.52546 (13) | 0.54907 (16) | 0.0795 (10) | |
H6 | 0.826003 | 0.517879 | 0.585166 | 0.095* | |
C7 | 0.8392 (5) | 0.57845 (14) | 0.52916 (17) | 0.0845 (11) | |
H7 | 0.880402 | 0.606465 | 0.551749 | 0.101* | |
C8 | 0.8110 (5) | 0.58998 (14) | 0.47617 (17) | 0.0843 (11) | |
H8 | 0.833890 | 0.625898 | 0.463070 | 0.101* | |
C9 | 0.7497 (5) | 0.54977 (13) | 0.44212 (16) | 0.0811 (10) | |
H9 | 0.729519 | 0.557999 | 0.406213 | 0.097* | |
C10 | 0.5992 (4) | 0.33085 (11) | 0.51677 (11) | 0.0512 (7) | |
C11 | 0.5060 (4) | 0.29166 (12) | 0.49111 (13) | 0.0590 (7) | |
H11 | 0.458704 | 0.296635 | 0.457296 | 0.071* | |
C12 | 0.6074 (4) | 0.26392 (11) | 0.57715 (12) | 0.0527 (7) | |
C13 | 0.6996 (4) | 0.26833 (11) | 0.67224 (12) | 0.0543 (7) | |
H13 | 0.622678 | 0.300241 | 0.677451 | 0.065* | |
C14 | 0.6679 (4) | 0.22431 (12) | 0.71584 (13) | 0.0623 (8) | |
H14A | 0.773301 | 0.210687 | 0.730791 | 0.075* | |
H14B | 0.599109 | 0.239701 | 0.744513 | 0.075* | |
C15 | 0.5765 (4) | 0.17823 (11) | 0.68671 (12) | 0.0549 (7) | |
C16 | 0.8778 (3) | 0.28972 (10) | 0.66887 (11) | 0.0484 (6) | |
C17 | 1.0059 (4) | 0.25844 (13) | 0.64682 (13) | 0.0647 (8) | |
H17 | 0.982862 | 0.222720 | 0.633272 | 0.078* | |
C18 | 1.1688 (5) | 0.27924 (19) | 0.64442 (16) | 0.0850 (11) | |
H18 | 1.255418 | 0.258144 | 0.629208 | 0.102* | |
C19 | 1.1984 (5) | 0.3308 (2) | 0.66472 (18) | 0.0861 (11) | |
C20 | 1.0797 (5) | 0.36238 (15) | 0.68832 (17) | 0.0872 (11) | |
H20 | 1.106018 | 0.397365 | 0.702961 | 0.105* | |
C21 | 0.9171 (4) | 0.34161 (11) | 0.69032 (14) | 0.0676 (9) | |
H21 | 0.832787 | 0.362996 | 0.706419 | 0.081* | |
C22 | 0.5073 (4) | 0.12765 (11) | 0.71181 (12) | 0.0539 (7) | |
C23 | 0.4302 (4) | 0.08538 (12) | 0.68196 (14) | 0.0683 (8) | |
H23 | 0.422286 | 0.088981 | 0.644896 | 0.082* | |
C24 | 0.3655 (5) | 0.03834 (13) | 0.70667 (15) | 0.0751 (10) | |
H24 | 0.314270 | 0.010204 | 0.686412 | 0.090* | |
C25 | 0.3768 (5) | 0.03306 (11) | 0.76113 (15) | 0.0700 (9) | |
C26 | 0.4514 (5) | 0.07388 (12) | 0.79203 (14) | 0.0706 (9) | |
H26 | 0.458289 | 0.069842 | 0.829072 | 0.085* | |
C27 | 0.5162 (4) | 0.12107 (12) | 0.76704 (13) | 0.0637 (8) | |
H27 | 0.566947 | 0.149040 | 0.787635 | 0.076* | |
N1 | 0.6574 (3) | 0.31478 (9) | 0.56682 (9) | 0.0545 (6) | |
N3 | 0.6491 (3) | 0.23679 (9) | 0.62379 (10) | 0.0629 (7) | |
N5 | 0.5655 (3) | 0.18683 (9) | 0.63576 (11) | 0.0607 (6) | |
O1 | 0.6566 (3) | 0.45689 (8) | 0.42704 (9) | 0.0774 (7) | |
O2 | 0.5641 (4) | 0.37238 (9) | 0.40796 (10) | 0.0963 (9) | |
S1 | 0.48577 (10) | 0.23142 (3) | 0.52875 (3) | 0.0601 (3) | |
Cl1 | 0.29654 (18) | −0.02666 (4) | 0.79278 (5) | 0.1103 (4) | |
F1 | 1.3583 (3) | 0.35259 (13) | 0.66200 (13) | 0.1451 (12) |
U11 | U22 | U33 | U12 | U13 | U23 | |
C1 | 0.101 (2) | 0.0501 (15) | 0.051 (2) | −0.0008 (16) | −0.0030 (17) | 0.0017 (14) |
C2 | 0.0635 (16) | 0.0520 (14) | 0.0427 (18) | 0.0052 (13) | 0.0025 (13) | 0.0007 (12) |
C3 | 0.078 (2) | 0.0568 (15) | 0.0448 (18) | −0.0010 (15) | −0.0017 (15) | −0.0005 (13) |
C4 | 0.0722 (19) | 0.0532 (15) | 0.057 (2) | 0.0002 (14) | 0.0046 (16) | 0.0007 (14) |
C5 | 0.081 (2) | 0.0504 (15) | 0.057 (2) | 0.0040 (15) | 0.0025 (16) | −0.0009 (14) |
C6 | 0.109 (3) | 0.0625 (19) | 0.067 (2) | −0.0128 (18) | −0.001 (2) | −0.0054 (16) |
C7 | 0.109 (3) | 0.0623 (19) | 0.082 (3) | −0.0137 (19) | −0.001 (2) | −0.0077 (18) |
C8 | 0.112 (3) | 0.0541 (17) | 0.087 (3) | −0.0056 (18) | 0.008 (2) | 0.0085 (18) |
C9 | 0.115 (3) | 0.0567 (17) | 0.071 (3) | −0.0001 (19) | −0.001 (2) | 0.0081 (16) |
C10 | 0.0621 (17) | 0.0509 (13) | 0.0404 (17) | 0.0058 (13) | −0.0005 (13) | −0.0007 (12) |
C11 | 0.0741 (19) | 0.0576 (16) | 0.0453 (18) | −0.0008 (14) | −0.0093 (14) | −0.0016 (13) |
C12 | 0.0600 (16) | 0.0534 (15) | 0.0447 (17) | −0.0003 (13) | −0.0018 (13) | 0.0017 (12) |
C13 | 0.0659 (17) | 0.0482 (13) | 0.0488 (18) | 0.0010 (13) | −0.0046 (13) | −0.0015 (12) |
C14 | 0.074 (2) | 0.0609 (16) | 0.052 (2) | −0.0109 (15) | −0.0033 (15) | 0.0034 (14) |
C15 | 0.0635 (17) | 0.0495 (14) | 0.052 (2) | −0.0002 (13) | −0.0052 (14) | 0.0013 (13) |
C16 | 0.0613 (16) | 0.0444 (13) | 0.0397 (16) | 0.0052 (12) | −0.0026 (12) | 0.0008 (11) |
C17 | 0.084 (2) | 0.0634 (17) | 0.0468 (19) | 0.0155 (16) | 0.0023 (15) | −0.0049 (14) |
C18 | 0.071 (2) | 0.119 (3) | 0.065 (3) | 0.031 (2) | 0.0178 (18) | 0.014 (2) |
C19 | 0.059 (2) | 0.111 (3) | 0.088 (3) | −0.009 (2) | −0.0010 (19) | 0.033 (2) |
C20 | 0.087 (3) | 0.068 (2) | 0.106 (3) | −0.022 (2) | −0.012 (2) | 0.003 (2) |
C21 | 0.071 (2) | 0.0489 (15) | 0.083 (3) | 0.0014 (15) | 0.0023 (18) | −0.0112 (14) |
C22 | 0.0671 (18) | 0.0478 (14) | 0.0468 (18) | 0.0010 (13) | −0.0023 (13) | 0.0013 (12) |
C23 | 0.095 (2) | 0.0564 (16) | 0.053 (2) | −0.0090 (17) | −0.0010 (17) | −0.0058 (14) |
C24 | 0.106 (3) | 0.0536 (16) | 0.066 (3) | −0.0150 (17) | 0.0013 (19) | −0.0111 (15) |
C25 | 0.092 (2) | 0.0509 (15) | 0.067 (2) | −0.0062 (16) | 0.0103 (18) | 0.0031 (15) |
C26 | 0.099 (2) | 0.0604 (17) | 0.052 (2) | −0.0064 (17) | 0.0027 (17) | 0.0030 (15) |
C27 | 0.081 (2) | 0.0543 (15) | 0.056 (2) | −0.0049 (14) | −0.0059 (16) | 0.0016 (14) |
N1 | 0.0670 (14) | 0.0523 (12) | 0.0442 (15) | −0.0023 (11) | −0.0048 (11) | 0.0024 (10) |
N3 | 0.0846 (17) | 0.0538 (13) | 0.0503 (16) | −0.0152 (12) | −0.0163 (13) | 0.0064 (11) |
N5 | 0.0790 (17) | 0.0497 (12) | 0.0534 (17) | −0.0092 (12) | −0.0080 (13) | 0.0029 (11) |
O1 | 0.125 (2) | 0.0554 (11) | 0.0522 (14) | −0.0044 (12) | −0.0058 (13) | 0.0056 (10) |
O2 | 0.172 (3) | 0.0663 (13) | 0.0507 (15) | −0.0200 (16) | −0.0255 (16) | 0.0004 (11) |
S1 | 0.0744 (5) | 0.0541 (4) | 0.0517 (5) | −0.0075 (3) | −0.0083 (4) | −0.0012 (3) |
Cl1 | 0.1708 (11) | 0.0635 (5) | 0.0965 (9) | −0.0316 (6) | 0.0262 (7) | 0.0075 (5) |
F1 | 0.0697 (14) | 0.196 (3) | 0.170 (3) | −0.0305 (16) | −0.0078 (16) | 0.066 (2) |
C1—O2 | 1.196 (4) | C14—C15 | 1.499 (4) |
C1—O1 | 1.386 (3) | C14—H14A | 0.9700 |
C1—C2 | 1.447 (4) | C14—H14B | 0.9700 |
C2—C3 | 1.351 (4) | C15—N5 | 1.289 (4) |
C2—C10 | 1.466 (4) | C15—C22 | 1.459 (4) |
C3—C4 | 1.427 (4) | C16—C17 | 1.372 (4) |
C3—H3 | 0.9300 | C16—C21 | 1.377 (4) |
C4—C5 | 1.381 (4) | C17—C18 | 1.383 (5) |
C4—C6 | 1.395 (4) | C17—H17 | 0.9300 |
C5—O1 | 1.377 (4) | C18—C19 | 1.344 (5) |
C5—C9 | 1.384 (4) | C18—H18 | 0.9300 |
C6—C7 | 1.375 (4) | C19—C20 | 1.338 (6) |
C6—H6 | 0.9300 | C19—F1 | 1.370 (4) |
C7—C8 | 1.367 (5) | C20—C21 | 1.380 (5) |
C7—H7 | 0.9300 | C20—H20 | 0.9300 |
C8—C9 | 1.366 (5) | C21—H21 | 0.9300 |
C8—H8 | 0.9300 | C22—C27 | 1.387 (4) |
C9—H9 | 0.9300 | C22—C23 | 1.390 (4) |
C10—C11 | 1.348 (4) | C23—C24 | 1.373 (4) |
C10—N1 | 1.384 (3) | C23—H23 | 0.9300 |
C11—S1 | 1.716 (3) | C24—C25 | 1.366 (5) |
C11—H11 | 0.9300 | C24—H24 | 0.9300 |
C12—N1 | 1.295 (3) | C25—C26 | 1.371 (4) |
C12—N3 | 1.369 (4) | C25—Cl1 | 1.741 (3) |
C12—S1 | 1.726 (3) | C26—C27 | 1.380 (4) |
C13—N3 | 1.476 (4) | C26—H26 | 0.9300 |
C13—C16 | 1.503 (4) | C27—H27 | 0.9300 |
C13—C14 | 1.528 (4) | N3—N5 | 1.389 (3) |
C13—H13 | 0.9800 | ||
O2—C1—O1 | 115.4 (3) | H14A—C14—H14B | 109.0 |
O2—C1—C2 | 127.1 (3) | N5—C15—C22 | 121.8 (3) |
O1—C1—C2 | 117.5 (3) | N5—C15—C14 | 113.2 (2) |
C3—C2—C1 | 119.2 (3) | C22—C15—C14 | 125.0 (3) |
C3—C2—C10 | 121.7 (3) | C17—C16—C21 | 118.1 (3) |
C1—C2—C10 | 119.1 (2) | C17—C16—C13 | 122.4 (3) |
C2—C3—C4 | 122.6 (3) | C21—C16—C13 | 119.5 (3) |
C2—C3—H3 | 118.7 | C16—C17—C18 | 121.0 (3) |
C4—C3—H3 | 118.7 | C16—C17—H17 | 119.5 |
C5—C4—C6 | 117.4 (3) | C18—C17—H17 | 119.5 |
C5—C4—C3 | 117.5 (3) | C19—C18—C17 | 118.1 (3) |
C6—C4—C3 | 125.1 (3) | C19—C18—H18 | 121.0 |
O1—C5—C4 | 120.8 (3) | C17—C18—H18 | 121.0 |
O1—C5—C9 | 116.9 (3) | C20—C19—C18 | 123.5 (3) |
C4—C5—C9 | 122.3 (3) | C20—C19—F1 | 117.5 (4) |
C7—C6—C4 | 120.6 (3) | C18—C19—F1 | 119.0 (4) |
C7—C6—H6 | 119.7 | C19—C20—C21 | 118.2 (3) |
C4—C6—H6 | 119.7 | C19—C20—H20 | 120.9 |
C8—C7—C6 | 120.1 (3) | C21—C20—H20 | 120.9 |
C8—C7—H7 | 120.0 | C16—C21—C20 | 121.1 (3) |
C6—C7—H7 | 120.0 | C16—C21—H21 | 119.5 |
C9—C8—C7 | 121.3 (3) | C20—C21—H21 | 119.5 |
C9—C8—H8 | 119.4 | C27—C22—C23 | 118.2 (3) |
C7—C8—H8 | 119.4 | C27—C22—C15 | 119.9 (3) |
C8—C9—C5 | 118.3 (3) | C23—C22—C15 | 121.9 (3) |
C8—C9—H9 | 120.8 | C24—C23—C22 | 120.7 (3) |
C5—C9—H9 | 120.8 | C24—C23—H23 | 119.7 |
C11—C10—N1 | 114.9 (2) | C22—C23—H23 | 119.7 |
C11—C10—C2 | 127.9 (3) | C25—C24—C23 | 119.7 (3) |
N1—C10—C2 | 117.2 (2) | C25—C24—H24 | 120.1 |
C10—C11—S1 | 111.4 (2) | C23—C24—H24 | 120.1 |
C10—C11—H11 | 124.3 | C24—C25—C26 | 121.4 (3) |
S1—C11—H11 | 124.3 | C24—C25—Cl1 | 120.1 (3) |
N1—C12—N3 | 122.2 (3) | C26—C25—Cl1 | 118.5 (3) |
N1—C12—S1 | 116.6 (2) | C25—C26—C27 | 118.7 (3) |
N3—C12—S1 | 121.2 (2) | C25—C26—H26 | 120.7 |
N3—C13—C16 | 112.3 (2) | C27—C26—H26 | 120.7 |
N3—C13—C14 | 101.0 (2) | C26—C27—C22 | 121.3 (3) |
C16—C13—C14 | 115.1 (2) | C26—C27—H27 | 119.3 |
N3—C13—H13 | 109.3 | C22—C27—H27 | 119.3 |
C16—C13—H13 | 109.3 | C12—N1—C10 | 109.5 (2) |
C14—C13—H13 | 109.3 | C12—N3—N5 | 117.9 (2) |
C15—C14—C13 | 103.5 (2) | C12—N3—C13 | 121.5 (2) |
C15—C14—H14A | 111.1 | N5—N3—C13 | 112.7 (2) |
C13—C14—H14A | 111.1 | C15—N5—N3 | 108.3 (2) |
C15—C14—H14B | 111.1 | C5—O1—C1 | 122.3 (3) |
C13—C14—H14B | 111.1 | C11—S1—C12 | 87.62 (14) |
D—H···A | D—H | H···A | D···A | D—H···A |
C13—H13···F1i | 0.98 | 2.47 | 3.372 (4) | 154 |
C20—H20···Cl1ii | 0.93 | 2.98 | 3.829 (4) | 153 |
C26—H26···O2iii | 0.93 | 2.54 | 3.282 (4) | 137 |
Symmetry codes: (i) x−1, y, z; (ii) −x+3/2, y+1/2, z; (iii) x, −y+1/2, z+1/2. |
Footnotes
‡Additional correspondence author, e-mail: kariukib@cardiff.ac.uk.
Acknowledgements
The authors thank Umm Al-Qura and Cardiff Universities for their support.
Funding information
Funding for this research was provided by: Deanship of Scientific Research at Umm Al-Qura University (award No. 17-MED-1-03-0007).
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