3-(3-Meth­oxy­benzo­yl)-1,1-diphenyl­thio­urea

Md Nasir, M.F.; Hassan, I.N.; Yamin, B.M.; Daud, W.R.W.; Kassim, M.B.

doi:10.1107/S1600536811025785

organic compounds

CRYSTALLOGRAPHIC
COMMUNICATIONS

ISSN: 2056-9890

Volume 67| Part 8| August 2011| Pages o1947-o1948

doi:10.1107/S1600536811025785

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3-(3-Methoxybenzoyl)-1,1-diphenylthiourea

Mohd Faizal Md Nasir,^a Ibrahim N. Hassan,^a Bohari M. Yamin,^b W. R. W Daud ^c,^a and Mohammad B. Kassim ^d,^a ^*

^aFuel Cell Institute, University Kebangsaan Malaysia, 43600 Selangor, Malaysia, ^bSchool of Chemical Sciences & Food Technology, Faculty of Science & Technology, University Kebangsaan Malaysia, 43600 Selangor, Malaysia, ^cDepartment of Chemical and Process Engineering, Faculty of Engineering and Built Environment, University Kebangsaan Malaysia, 43600 Selangor, Malaysia, and ^dSchool of Chemical Sciences & Food Technology, Faculty of Science & Technology, University Kebangsaan Malaysia, 43600 Selangor, Malaysia
^*Correspondence e-mail: mbkassim@ukm.my

(Received 29 June 2011; accepted 29 June 2011; online 9 July 2011)

The thiono and carbonyl groups in the title compound, C₂₁H₁₈N₂O₂S, adopt an anti disposition with respect to the central C—N bond. The diphenylamine rings are twisted relative to each other by a dihedral angle of 82.55 (10)°. The 3-methoxybenzoyl fragment is twisted relative to one of the diphenylamine rings, forming a dihedral angle of 74.04 (9)°. In the crystal, pairs of intermolecular N—H⋯S hydrogen bonds link the molecules into centrosymmetric dimers, forming columns parallel to the a axis.

Related literature

For related structures and background references, see: Al-abbasi et al. (2010 ); Al-abbasi & Kassim (2011 ); Md Nasir et al. (2011 ). For metal complexes of benzoylthioureas, see: Circu et al. (2009 ); Weiqun et al. (2005 ). For the synthetic procedure, see: Hassan et al. (2008 ). For a standard bond lengths, see: Allen et al. (1987 ).

Experimental

Crystal data

C₂₁H₁₈N₂O₂S
M_r = 362.43
Triclinic, $[P \overline 1]$
a = 6.056 (3) Å
b = 12.895 (7) Å
c = 13.344 (7) Å
α = 112.796 (9)°
β = 100.336 (10)°
γ = 97.951 (10)°
V = 920.0 (8) Å³
Z = 2
Mo Kα radiation
μ = 0.19 mm⁻¹
T = 298 K
0.52 × 0.23 × 0.03 mm

Data collection

Bruker SMART APEX CCD area-detector diffractometer
Absorption correction: multi-scan (SADABS; Bruker, 2000 ) T_min = 0.906, T_max = 0.994
10189 measured reflections
3612 independent reflections
2663 reflections with I > 2σ(I)
R_int = 0.029

Refinement

R[F² > 2σ(F²)] = 0.038
wR(F²) = 0.110
S = 1.04
3612 reflections
240 parameters
H atoms treated by a mixture of independent and constrained refinement
Δρ_max = 0.17 e Å⁻³
Δρ_min = −0.27 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N1—H1A⋯S1ⁱ	0.87 (2)	2.54 (2)	3.380 (2)	163.6 (17)
Symmetry code: (i) -x+1, -y+1, -z+1.

Data collection: SMART (Bruker, 2000); cell refinement: SAINT (Bruker, 2000); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: SHELXTL (Sheldrick, 2008); software used to prepare material for publication: SHELXTL and PLATON (Spek, 2009 ).

Supporting information

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536811025785/jh2306sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536811025785/jh2306Isup2.hkl

Supporting information file. DOI: 10.1107/S1600536811025785/jh2306Isup3.cml

checkCIF report

Comment top

Benzoylthiourea compounds act as a chelating ligands by deprotonation of the amide group and coordinate via a thiolate form through the S and O atoms to form neutral complexes with cobalt (Weiqun et al., 2005) and platinum (Circu et al., 2009).

The title compound, I, is a thiourea derivative analogous to our previously reported compounds (Md Nasir et al., 2011; Al-abbasi & Kassim, 2011). The thiono and the carbonyl groups are trans positioned with respect to N1—C8 bond with C7N1C8S1 torsion angle of -129.10 (16)°. The methoxy group is coplanar with the parent benzene ring with the largest deviation from the mean planes of (O1/C1/C2/C3/C4/C5/C6/C7) of -0.051 (2)° for C7 and the dihedral angle between the same plane and the thioamide mean planes (S1/N1/N2/C8) is 87.45 (8)°.

In the crystal structure, Intermolecular N1—H1A···S1 hydrogen bond link the molecules into a centrosymmetric dimers forming channel parallel to the a-axis.

Related literature top

For related structures and background references, see: Al-abbasi et al. (2010); Al-abbasi & Kassim (2011); Md Nasir et al. (2011). For metal complexes of benzoylthioureas, see: Circu et al. (2009); Weiqun et al. (2005). For the synthetic procedure, see: Hassan et al. (2008). For a standard bond lengths, see: Allen et al. (1987).

Experimental top

The title compound was prepared according to a previously reported procedure (Al-abbasi et al., 2010) using 3-methoxybenzoyl chloride and diphenylamine as the appropriate starting materials. A yellowish crystal, suitable for X-ray crystallography, was obtained by a slow evaporation from ethanol solution at room temperature (yield 75%).

Computing details top

Data collection: SMART (Bruker, 2000); cell refinement: SAINT (Bruker, 2000); data reduction: SAINT (Bruker, 2000); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: SHELXTL (Sheldrick, 2008); software used to prepare material for publication: SHELXTL (Sheldrick, 2008) and PLATON (Spek, 2009).

Figures top

	Fig. 1. The molecular structure of the title compound with displacement ellipsoids drawn at the 50% probability level.
	Fig. 2. A packing diagram of the title compound viewed down the a-axis showing the intermolecular hydrogen bonds N1—H1···S1 (-x + 1, -y + 1, -z + 1) centrosymmetric dimers along a-axis.

3-(3-Methoxybenzoyl)-1,1-diphenylthiourea top

Crystal data top

C₂₁H₁₈N₂O₂S	Z = 2
M_r = 362.43	F(000) = 380
Triclinic, P1	D_x = 1.308 Mg m⁻³
Hall symbol: -P 1	Melting point = 412.15–410.15 K
a = 6.056 (3) Å	Mo Kα radiation, λ = 0.71073 Å
b = 12.895 (7) Å	Cell parameters from 3612 reflections
c = 13.344 (7) Å	θ = 6.4–55.2°
α = 112.796 (9)°	µ = 0.19 mm⁻¹
β = 100.336 (10)°	T = 298 K
γ = 97.951 (10)°	Plate, yellow
V = 920.0 (8) Å³	0.52 × 0.23 × 0.03 mm

Data collection top

Bruker SMART APEX CCD area-detector diffractometer	3612 independent reflections
Radiation source: fine-focus sealed tube	2663 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.029
ω scan	θ_max = 26.0°, θ_min = 1.7°
Absorption correction: multi-scan (SADABS; Bruker, 2000)	h = −7→7
T_min = 0.906, T_max = 0.994	k = −15→15
10189 measured reflections	l = −16→16

Refinement top

Refinement on F²	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F² > 2σ(F²)] = 0.038	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.110	H atoms treated by a mixture of independent and constrained refinement
S = 1.04	w = 1/[σ²(F_o²) + (0.0578P)² + 0.1546P] where P = (F_o² + 2F_c²)/3
3612 reflections	(Δ/σ)_max < 0.001
240 parameters	Δρ_max = 0.17 e Å⁻³
0 restraints	Δρ_min = −0.27 e Å⁻³

Crystal data top

C₂₁H₁₈N₂O₂S	γ = 97.951 (10)°
M_r = 362.43	V = 920.0 (8) Å³
Triclinic, P1	Z = 2
a = 6.056 (3) Å	Mo Kα radiation
b = 12.895 (7) Å	µ = 0.19 mm⁻¹
c = 13.344 (7) Å	T = 298 K
α = 112.796 (9)°	0.52 × 0.23 × 0.03 mm
β = 100.336 (10)°

Data collection top

Bruker SMART APEX CCD area-detector diffractometer	3612 independent reflections
Absorption correction: multi-scan (SADABS; Bruker, 2000)	2663 reflections with I > 2σ(I)
T_min = 0.906, T_max = 0.994	R_int = 0.029
10189 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.038	0 restraints
wR(F²) = 0.110	H atoms treated by a mixture of independent and constrained refinement
S = 1.04	Δρ_max = 0.17 e Å⁻³
3612 reflections	Δρ_min = −0.27 e Å⁻³
240 parameters

Special details top

Geometry. All e.s.d.'s (except the e.s.d. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell e.s.d.'s are taken into account individually in the estimation of e.s.d.'s in distances, angles and torsion angles; correlations between e.s.d.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell e.s.d.'s is used for estimating e.s.d.'s 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 > σ(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.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å²) top

	x	y	z	U_iso*/U_eq
S1	0.28578 (10)	0.32442 (4)	0.43411 (4)	0.05684 (19)
O1	0.0958 (3)	0.92764 (11)	0.40494 (14)	0.0667 (4)
O2	−0.0666 (2)	0.49768 (10)	0.27758 (12)	0.0554 (4)
N1	0.2897 (3)	0.47668 (11)	0.34630 (12)	0.0403 (4)
N2	0.0990 (2)	0.28974 (11)	0.22465 (10)	0.0372 (3)
C6	0.4600 (3)	0.67429 (15)	0.30353 (15)	0.0458 (4)
H6	0.5408	0.6164	0.2821	0.055*
C5	0.5442 (3)	0.78217 (16)	0.30918 (17)	0.0504 (5)
H5	0.6817	0.7962	0.2898	0.060*
C4	0.4287 (3)	0.86899 (15)	0.34293 (15)	0.0458 (4)
H4	0.4889	0.9413	0.3471	0.055*
C3	0.2235 (3)	0.84874 (14)	0.37065 (15)	0.0438 (4)
C2	0.1354 (3)	0.74050 (14)	0.36416 (14)	0.0430 (4)
H2	−0.0031	0.7264	0.3827	0.052*
C1	0.2519 (3)	0.65424 (13)	0.33049 (13)	0.0380 (4)
C21	0.1482 (4)	1.03154 (16)	0.39139 (19)	0.0595 (5)
H21A	0.2992	1.0754	0.4378	0.089*
H21B	0.0366	1.0762	0.4132	0.089*
H21C	0.1443	1.0132	0.3141	0.089*
C7	0.1389 (3)	0.53717 (14)	0.31542 (14)	0.0405 (4)
C8	0.2192 (3)	0.36345 (13)	0.33048 (13)	0.0376 (4)
C9	0.1204 (3)	0.31150 (13)	0.12858 (13)	0.0369 (4)
C14	−0.0742 (3)	0.29310 (16)	0.04667 (14)	0.0476 (4)
H14	−0.2192	0.2659	0.0529	0.057*
C13	−0.0526 (4)	0.31537 (19)	−0.04475 (16)	0.0610 (6)
H13	−0.1836	0.3029	−0.1002	0.073*
C12	0.1610 (4)	0.35575 (19)	−0.05447 (17)	0.0618 (6)
H12	0.1745	0.3719	−0.1155	0.074*
C11	0.3535 (4)	0.37199 (18)	0.02626 (18)	0.0579 (5)
H11	0.4983	0.3987	0.0195	0.070*
C10	0.3355 (3)	0.34923 (15)	0.11738 (15)	0.0464 (4)
H10	0.4675	0.3592	0.1712	0.056*
C15	−0.0664 (3)	0.18826 (13)	0.20578 (13)	0.0388 (4)
C16	−0.2480 (3)	0.20071 (17)	0.25501 (16)	0.0523 (5)
H16	−0.2582	0.2736	0.3035	0.063*
C17	−0.4148 (4)	0.1046 (2)	0.2320 (2)	0.0697 (6)
H17	−0.5374	0.1125	0.2654	0.084*
C18	−0.4001 (4)	−0.0022 (2)	0.16034 (19)	0.0757 (8)
H18	−0.5141	−0.0668	0.1442	0.091*
C19	−0.2184 (4)	−0.01469 (17)	0.11210 (17)	0.0691 (7)
H19	−0.2089	−0.0879	0.0640	0.083*
C20	−0.0481 (4)	0.08113 (14)	0.13453 (14)	0.0505 (5)
H20	0.0756	0.0729	0.1020	0.061*
H1A	0.416 (3)	0.5170 (16)	0.3974 (17)	0.049 (5)*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
S1	0.0816 (4)	0.0375 (2)	0.0398 (3)	−0.0063 (2)	−0.0094 (2)	0.02171 (19)
O1	0.0816 (11)	0.0378 (7)	0.1021 (12)	0.0228 (7)	0.0492 (9)	0.0372 (7)
O2	0.0428 (8)	0.0374 (7)	0.0779 (9)	0.0029 (6)	0.0069 (7)	0.0217 (6)
N1	0.0461 (9)	0.0274 (7)	0.0387 (7)	−0.0018 (6)	−0.0051 (7)	0.0153 (6)
N2	0.0446 (8)	0.0302 (7)	0.0328 (7)	0.0003 (6)	0.0040 (6)	0.0142 (5)
C6	0.0488 (11)	0.0418 (9)	0.0496 (10)	0.0113 (8)	0.0086 (8)	0.0238 (8)
C5	0.0430 (10)	0.0521 (11)	0.0630 (12)	0.0058 (9)	0.0131 (9)	0.0333 (9)
C4	0.0488 (11)	0.0375 (9)	0.0517 (10)	0.0015 (8)	0.0055 (8)	0.0253 (8)
C3	0.0518 (11)	0.0335 (9)	0.0469 (9)	0.0085 (8)	0.0110 (8)	0.0188 (7)
C2	0.0461 (10)	0.0367 (9)	0.0495 (10)	0.0072 (8)	0.0132 (8)	0.0218 (8)
C1	0.0430 (10)	0.0328 (8)	0.0361 (8)	0.0026 (7)	0.0026 (7)	0.0176 (7)
C21	0.0784 (15)	0.0376 (10)	0.0712 (13)	0.0151 (10)	0.0196 (11)	0.0313 (10)
C7	0.0489 (11)	0.0310 (8)	0.0379 (8)	0.0046 (7)	0.0078 (7)	0.0137 (7)
C8	0.0401 (9)	0.0309 (8)	0.0372 (8)	0.0020 (7)	0.0029 (7)	0.0147 (7)
C9	0.0448 (10)	0.0315 (8)	0.0334 (8)	0.0053 (7)	0.0072 (7)	0.0152 (6)
C14	0.0459 (11)	0.0524 (10)	0.0402 (9)	0.0039 (8)	0.0045 (8)	0.0205 (8)
C13	0.0669 (14)	0.0732 (13)	0.0408 (10)	0.0146 (11)	0.0008 (9)	0.0283 (10)
C12	0.0808 (16)	0.0711 (14)	0.0466 (11)	0.0179 (12)	0.0230 (11)	0.0353 (10)
C11	0.0609 (13)	0.0614 (12)	0.0640 (12)	0.0120 (10)	0.0276 (10)	0.0350 (10)
C10	0.0463 (11)	0.0460 (10)	0.0472 (10)	0.0078 (8)	0.0090 (8)	0.0223 (8)
C15	0.0432 (10)	0.0341 (8)	0.0340 (8)	−0.0015 (7)	0.0017 (7)	0.0162 (7)
C16	0.0512 (12)	0.0517 (11)	0.0542 (11)	0.0064 (9)	0.0130 (9)	0.0247 (9)
C17	0.0547 (13)	0.0831 (16)	0.0705 (14)	−0.0078 (12)	0.0141 (11)	0.0403 (13)
C18	0.0862 (17)	0.0643 (14)	0.0560 (12)	−0.0330 (12)	0.0002 (12)	0.0286 (11)
C19	0.1047 (19)	0.0375 (10)	0.0451 (11)	−0.0142 (11)	0.0102 (12)	0.0110 (8)
C20	0.0684 (13)	0.0364 (9)	0.0386 (9)	0.0007 (9)	0.0121 (9)	0.0118 (7)

Geometric parameters (Å, º) top

S1—C8	1.6503 (17)	C21—H21C	0.9600
O1—C3	1.351 (2)	C9—C14	1.378 (2)
O1—C21	1.421 (2)	C9—C10	1.381 (3)
O2—C7	1.210 (2)	C14—C13	1.381 (3)
N1—C8	1.384 (2)	C14—H14	0.9300
N1—C7	1.387 (2)	C13—C12	1.373 (3)
N1—H1A	0.87 (2)	C13—H13	0.9300
N2—C8	1.352 (2)	C12—C11	1.368 (3)
N2—C9	1.438 (2)	C12—H12	0.9300
N2—C15	1.439 (2)	C11—C10	1.375 (3)
C6—C5	1.382 (2)	C11—H11	0.9300
C6—C1	1.389 (3)	C10—H10	0.9300
C6—H6	0.9300	C15—C20	1.374 (3)
C5—C4	1.373 (3)	C15—C16	1.376 (3)
C5—H5	0.9300	C16—C17	1.377 (3)
C4—C3	1.378 (3)	C16—H16	0.9300
C4—H4	0.9300	C17—C18	1.365 (4)
C3—C2	1.387 (2)	C17—H17	0.9300
C2—C1	1.371 (3)	C18—C19	1.369 (4)
C2—H2	0.9300	C18—H18	0.9300
C1—C7	1.489 (2)	C19—C20	1.389 (3)
C21—H21A	0.9600	C19—H19	0.9300
C21—H21B	0.9600	C20—H20	0.9300

C3—O1—C21	118.49 (16)	C14—C9—C10	119.92 (16)
C8—N1—C7	122.68 (15)	C14—C9—N2	119.86 (15)
C8—N1—H1A	116.5 (13)	C10—C9—N2	120.21 (15)
C7—N1—H1A	117.1 (13)	C9—C14—C13	119.56 (18)
C8—N2—C9	122.38 (13)	C9—C14—H14	120.2
C8—N2—C15	119.92 (13)	C13—C14—H14	120.2
C9—N2—C15	117.62 (12)	C12—C13—C14	120.52 (19)
C5—C6—C1	118.54 (17)	C12—C13—H13	119.7
C5—C6—H6	120.7	C14—C13—H13	119.7
C1—C6—H6	120.7	C11—C12—C13	119.54 (18)
C4—C5—C6	121.22 (18)	C11—C12—H12	120.2
C4—C5—H5	119.4	C13—C12—H12	120.2
C6—C5—H5	119.4	C12—C11—C10	120.76 (19)
C5—C4—C3	119.88 (16)	C12—C11—H11	119.6
C5—C4—H4	120.1	C10—C11—H11	119.6
C3—C4—H4	120.1	C11—C10—C9	119.66 (18)
O1—C3—C4	124.89 (15)	C11—C10—H10	120.2
O1—C3—C2	115.53 (16)	C9—C10—H10	120.2
C4—C3—C2	119.57 (17)	C20—C15—C16	120.88 (16)
C1—C2—C3	120.20 (17)	C20—C15—N2	119.82 (16)
C1—C2—H2	119.9	C16—C15—N2	119.20 (16)
C3—C2—H2	119.9	C15—C16—C17	119.6 (2)
C2—C1—C6	120.58 (15)	C15—C16—H16	120.2
C2—C1—C7	117.72 (16)	C17—C16—H16	120.2
C6—C1—C7	121.53 (16)	C18—C17—C16	120.1 (2)
O1—C21—H21A	109.5	C18—C17—H17	120.0
O1—C21—H21B	109.5	C16—C17—H17	120.0
H21A—C21—H21B	109.5	C17—C18—C19	120.30 (19)
O1—C21—H21C	109.5	C17—C18—H18	119.9
H21A—C21—H21C	109.5	C19—C18—H18	119.9
H21B—C21—H21C	109.5	C18—C19—C20	120.5 (2)
O2—C7—N1	123.01 (15)	C18—C19—H19	119.8
O2—C7—C1	122.65 (16)	C20—C19—H19	119.8
N1—C7—C1	114.33 (15)	C15—C20—C19	118.6 (2)
N2—C8—N1	114.68 (14)	C15—C20—H20	120.7
N2—C8—S1	124.04 (12)	C19—C20—H20	120.7
N1—C8—S1	121.26 (12)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1A···S1ⁱ	0.87 (2)	2.54 (2)	3.380 (2)	163.6 (17)

Symmetry code: (i) −x+1, −y+1, −z+1.

Experimental details

Crystal data
Chemical formula	C₂₁H₁₈N₂O₂S
M_r	362.43
Crystal system, space group	Triclinic, P1
Temperature (K)	298
a, b, c (Å)	6.056 (3), 12.895 (7), 13.344 (7)
α, β, γ (°)	112.796 (9), 100.336 (10), 97.951 (10)
V (Å³)	920.0 (8)
Z	2
Radiation type	Mo Kα
µ (mm⁻¹)	0.19
Crystal size (mm)	0.52 × 0.23 × 0.03

Data collection
Diffractometer	Bruker SMART APEX CCD area-detector diffractometer
Absorption correction	Multi-scan (SADABS; Bruker, 2000)
T_min, T_max	0.906, 0.994
No. of measured, independent and observed [I > 2σ(I)] reflections	10189, 3612, 2663
R_int	0.029
(sin θ/λ)_max (Å⁻¹)	0.617

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.038, 0.110, 1.04
No. of reflections	3612
No. of parameters	240
H-atom treatment	H atoms treated by a mixture of independent and constrained refinement
Δρ_max, Δρ_min (e Å⁻³)	0.17, −0.27

Computer programs: SMART (Bruker, 2000), SAINT (Bruker, 2000), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), SHELXTL (Sheldrick, 2008) and PLATON (Spek, 2009).

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1A···S1ⁱ	0.87 (2)	2.54 (2)	3.380 (2)	163.6 (17)

Symmetry code: (i) −x+1, −y+1, −z+1.

Acknowledgements

The authors thank University Kebangsaan Malaysia for grants UKM-GUP-BTT-07–30-190 and UKM-OUP-TK-16–73/2010 and UKM-PTS-016–2009 and sabbatical leave for MBK, and the Kementerian Pengajian Tinggi, Malaysia, for the research fund No. UKM-ST-06-FRGS0111–2009.

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