(2E)-3-(4-Chloro­phen­yl)-1-(1H-pyrrol-2-yl)prop-2-en-1-one

Bukhari, M.H.; Siddiqui, H.L.; Tahir, M.N.; Chaudhary, M.A.; Iqbal, A.

doi:10.1107/S1600536808010362

organic compounds

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ISSN: 2056-9890

Volume 64| Part 5| May 2008| Pages o867-o868

doi:10.1107/S1600536808010362

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(2E)-3-(4-Chlorophenyl)-1-(1H-pyrrol-2-yl)prop-2-en-1-one

Mujahid Hussain Bukhari,^a Hamid Latif Siddiqui,^a M. Nawaz Tahir,^b ^* Muhammad Ashraf Chaudhary ^c and Amjid Iqbal ^a

^aInstitute of Chemistry, University of the Punjab, Lahore 54590, Pakistan, ^bUniversity of Sargodha, Department of Physics, Sargodha, Pakistan, and ^cDepartment of Chemistry, F.C. University, Lahore 54600, Pakistan
^*Correspondence e-mail: dmntahir_uos@yahoo.com

(Received 12 April 2008; accepted 15 April 2008; online 18 April 2008)

In the molecule of the title compound, C₁₃H₁₀ClNO, the benzene and pyrrole rings are oriented at a dihedral angle of 7.37 (12)°. In the crystal structure, intermolecular N—H⋯O hydrogen bonds link the molecules into centrosymmetric R₂²(10) dimers. There are C—H⋯π interactions between benzene and pyrrole rings and a benzene C—H group. A weak π–π interaction between the pyrrole rings [centroid–centroid distance 3.8515 (11) Å] further stabilizes the structure. There is also a π interaction between the pyrrole ring and the carbonyl group, with a carbon–centroid distance of 3.4825 (18) Å.

Related literature

For general background, see: Varga et al. (2003 ); Katritzky & Rees (1984 ); Wu et al. (2003 ); Nam et al. (2003 ); Sondhi et al. (2005 ); Miyazaki et al. (2005 ). For related literature, see: Powers et al. (1998 ); Hu et al. (2006 ); Wang et al. (2005 ); Zeng & Cen (2006 ). For ring motif details, see: Bernstein et al. (1995 ).

Experimental

Crystal data

C₁₃H₁₀ClNO
M_r = 231.67
Monoclinic, P 2₁ /c
a = 13.0401 (7) Å
b = 5.6326 (3) Å
c = 15.6857 (8) Å
β = 94.979 (3)°
V = 1147.76 (10) Å³
Z = 4
Mo Kα radiation
μ = 0.31 mm⁻¹
T = 296 (2) K
0.30 × 0.22 × 0.20 mm

Data collection

Bruker Kappa APEXII CCD diffractometer
Absorption correction: multi-scan (SADABS; Bruker, 2005 ) T_min = 0.903, T_max = 0.935
13745 measured reflections
3081 independent reflections
2180 reflections with I > 2σ(I)
R_int = 0.026

Refinement

R[F² > 2σ(F²)] = 0.043
wR(F²) = 0.128
S = 1.02
3081 reflections
185 parameters
All H-atom parameters refined
Δρ_max = 0.29 e Å⁻³
Δρ_min = −0.30 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N1—H1⋯O1ⁱ	0.83 (2)	2.12 (2)	2.902 (2)	156 (2)
C3—H3⋯CgAⁱⁱ	0.938 (18)	2.897 (17)	3.6339 (19)	136.4 (13)
C6—H6⋯CgBⁱⁱⁱ	0.94 (2)	2.651 (19)	3.4017 (19)	137.8 (16)
Symmetry codes: (i) -x, -y+1, -z+1; (ii) $[-x+1, y-{\script{1\over 2}}, -z+{\script{1\over 2}}]$ ; (iii) $[x, -y-{\script{1\over 2}}, z-{\script{3\over 2}}]$ . CgA and CgB are the centroids of the C1–C6 and N1/C10–C13 rings, respectively.

Data collection: APEX2 (Bruker, 2007 ); cell refinement: APEX2; data reduction: SAINT (Bruker, 2007); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: ORTEP-3 for Windows (Farrugia, 1997 ) and PLATON (Spek, 2003 ); software used to prepare material for publication: WinGX (Farrugia, 1999 ) and PLATON.

Supporting information

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536808010362/hk2452sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536808010362/hk2452Isup2.hkl

checkCIF report

Comment top

Chalcones are 1,3-diaryl α,β-unsaturated compounds commonly used as starting materials for the synthesis of several biologically active compounds like pyrimidines and imidazoles (Varga et al., 2003). Most of the chalcones and their derivatives show biological activities such as antimicrobial (Katritzky & Rees, 1984), anti-AIDS (Wu et al., 2003), antimalarial (Nam et al., 2003), anti-inflammatory and analgesic (Sondhi et al., 2005) and antitumor (Miyazaki et al., 2005). While synthesizing different pyrimidine based compounds, we prepared the fine crystals of the title compound, (I), with known method (Powers et al., 1998). We report herein its crystal structure.

The crystal structures of 3-(4-chlorophenyl)-1-(3,4-dimethyl-2,5-dihydro-1H- pyrrol-1-yl)prop-2-enone, (II) (Hu et al., 2006), methyl-3-(1H-pyrrol-2-yl- carboxamido)propionate, (III) (Zeng & Cen, 2006) and 1,3-bis(4-chlorophenyl)- prop-2-en-1-one, (IV) (Wang et al., 2005) have been reported, previously. The title compound, (I), contains the moieties involved in these reported structures.

In the molecule of (I), (Fig. 1), the bond lengths N1-C10 [1.3711 (19) Å], N1-C13 [1.338 (3) Å] and C11-C12 [1.388 (3) Å] are reported as 1.457 (5), 1.461 (5) and 1.328 (6) Å in (II) and 1.369 (2), 1.349 (3) and 1.398 (3) Å in (III), respectively. Rings A (C1-C6) and B (N1/C10-C13) are, of course, planar and they are oriented at a dihedral angle of 7.37 (12)°. So, they are nearly coplanar. The planar central moiety (O1/C7-C9) is oriented with respect to rings A and B at dihedral angles of 8.92 (12)° and 1.94 (15)°, respectively.

In the crystal structure, intermolecular N-H···O hydrogen bonds (Table 1) link the molecules into centrosymmetric R₂²(10) dimers (Fig. 2) (Bernstein et al., 1995), in which they may be effective in the stabilization of the structure. The C—H···π interactions (Table 1) and π—π interactions between B rings CgB···CgB^iv [symmetry code: (iv) -x, -y, 1 - z] further stabilize the structure, with a centroid-centroid distance of 3.8515 (11) Å. There is also a π interaction between the ring B at -x, -y, 1 - z and the carbonyl moiety, with C9-centroid distance of 3.4825 (18) Å.

Related literature top

For general background, see: Varga et al. (2003); Katritzky & Rees (1984); Wu et al. (2003); Nam et al. (2003); Sondhi et al. (2005); Miyazaki et al. (2005). For related literature, see: Powers et al. (1998); Hu et al. (2006); Wang et al. (2005); Zeng & Cen (2006). For ring motif details, see: Bernstein et al. (1995).

Experimental top

For the preparation of the title compound, a mixture of 4-chlorobenzaldehyde (1.4 g, 10 mmol) and 2-acetyl pyrrole (1.09 g, 10 mmol) was added to MeOH (20 ml) and stirred for 10 min at room temperature. Then, aqueous NaOH solution (10%, 4 ml) was added dropwise with continuous stirring at ambient temperature for 30 min. Light yellow precipitates appeared, to which cold water (40 ml) was added. Yellow colored powder was obtained from the filtrate, which was washed with cold MeOH, and then dried. The residue was recrystallized by dissolving in CHCl₃ (10 ml) and adding n-hexane dropwise. Fine yellow crystals were obtained (yield; 1.7 g, 73%, m.p. 420-422 K).

Computing details top

Data collection: APEX2 (Bruker, 2007); cell refinement: APEX2 (Bruker, 2007); data reduction: SAINT (Bruker, 2007); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: ORTEP-3 for Windows (Farrugia, 1997) and PLATON (Spek, 2003); software used to prepare material for publication: WinGX (Farrugia, 1999) and PLATON (Spek, 2003).

Figures top

	Fig. 1. The molecular structure of the title molecule, with the atom-numbering scheme. Displacement ellipsoids are drawn at the 50% probability level.
	Fig. 2. A partial packing diagram of (I), showing the formation of centro- symmetric R₂²(10) ring motifs. Hydrogen bonds are shown as dashed lines.

(2E)-3-(4-Chlorophenyl)-1-(1H-pyrrol-2-yl)prop-2-en-1-one top

Crystal data top

C₁₃H₁₀ClNO	F(000) = 480
M_r = 231.67	D_x = 1.341 Mg m⁻³
Monoclinic, P2₁/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 2883 reflections
a = 13.0401 (7) Å	θ = 2.4–28.7°
b = 5.6326 (3) Å	µ = 0.31 mm⁻¹
c = 15.6857 (8) Å	T = 296 K
β = 94.979 (3)°	Prismatic, light yellow
V = 1147.76 (10) Å³	0.30 × 0.22 × 0.20 mm
Z = 4

Data collection top

Bruker KappaAPEXII CCD diffractometer	3081 independent reflections
Radiation source: fine-focus sealed tube	2180 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.026
Detector resolution: 7.30 pixels mm^-1	θ_max = 29.1°, θ_min = 1.6°
ω scans	h = −17→17
Absorption correction: multi-scan (SADABS; Bruker, 2005)	k = −7→7
T_min = 0.903, T_max = 0.935	l = −21→21
13745 measured reflections

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)] = 0.043	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.128	All H-atom parameters refined
S = 1.02	w = 1/[σ²(F_o²) + (0.0533P)² + 0.3294P] where P = (F_o² + 2F_c²)/3
3081 reflections	(Δ/σ)_max < 0.001
185 parameters	Δρ_max = 0.29 e Å⁻³
0 restraints	Δρ_min = −0.30 e Å⁻³

Crystal data top

C₁₃H₁₀ClNO	V = 1147.76 (10) Å³
M_r = 231.67	Z = 4
Monoclinic, P2₁/c	Mo Kα radiation
a = 13.0401 (7) Å	µ = 0.31 mm⁻¹
b = 5.6326 (3) Å	T = 296 K
c = 15.6857 (8) Å	0.30 × 0.22 × 0.20 mm
β = 94.979 (3)°

Data collection top

Bruker KappaAPEXII CCD diffractometer	3081 independent reflections
Absorption correction: multi-scan (SADABS; Bruker, 2005)	2180 reflections with I > 2σ(I)
T_min = 0.903, T_max = 0.935	R_int = 0.026
13745 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.043	0 restraints
wR(F²) = 0.128	All H-atom parameters refined
S = 1.02	Δρ_max = 0.29 e Å⁻³
3081 reflections	Δρ_min = −0.30 e Å⁻³
185 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 > 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.

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

	x	y	z	U_iso*/U_eq
Cl	0.47349 (5)	−0.30082 (12)	0.06812 (4)	0.0972 (3)
O1	0.10949 (10)	0.4232 (2)	0.43283 (8)	0.0672 (4)
N1	0.05564 (11)	0.2306 (3)	0.58749 (10)	0.0572 (4)
C1	0.29765 (11)	0.0517 (3)	0.26744 (10)	0.0464 (3)
C2	0.34920 (13)	−0.1623 (3)	0.28485 (11)	0.0525 (4)
C3	0.40411 (13)	−0.2692 (3)	0.22394 (12)	0.0566 (4)
C4	0.40726 (13)	−0.1631 (3)	0.14559 (11)	0.0563 (4)
C5	0.35867 (14)	0.0498 (3)	0.12645 (11)	0.0588 (4)
C6	0.30445 (13)	0.1551 (3)	0.18805 (11)	0.0537 (4)
C7	0.23600 (12)	0.1706 (3)	0.32855 (10)	0.0503 (4)
C8	0.20870 (13)	0.0873 (3)	0.40137 (11)	0.0548 (4)
C9	0.14204 (12)	0.2253 (3)	0.45499 (11)	0.0522 (4)
C10	0.11764 (11)	0.1179 (3)	0.53393 (10)	0.0501 (4)
C11	0.14707 (13)	−0.0945 (3)	0.57282 (11)	0.0566 (4)
C12	0.10275 (15)	−0.1076 (4)	0.65000 (13)	0.0659 (5)
C13	0.04627 (14)	0.0958 (4)	0.65667 (12)	0.0668 (5)
H2	0.3481 (14)	−0.236 (3)	0.3387 (13)	0.066 (5)*
H3	0.4387 (13)	−0.413 (3)	0.2358 (11)	0.062 (5)*
H6	0.2713 (14)	0.300 (4)	0.1763 (12)	0.063 (5)*
H5	0.3607 (15)	0.124 (4)	0.0702 (14)	0.075 (6)*
H7	0.2116 (14)	0.324 (4)	0.3102 (12)	0.067 (5)*
H8	0.2289 (15)	−0.069 (4)	0.4203 (13)	0.076 (6)*
H1	0.0220 (17)	0.353 (4)	0.5749 (14)	0.073 (6)*
H11	0.1896 (14)	−0.211 (3)	0.5521 (12)	0.063 (5)*
H12	0.1118 (15)	−0.226 (4)	0.6931 (14)	0.075 (6)*
H13	0.0089 (17)	0.150 (4)	0.7011 (15)	0.091 (7)*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
Cl	0.1189 (5)	0.0979 (5)	0.0810 (4)	0.0298 (3)	0.0442 (3)	−0.0182 (3)
O1	0.0738 (8)	0.0584 (7)	0.0716 (8)	0.0223 (6)	0.0185 (6)	−0.0044 (6)
N1	0.0521 (7)	0.0644 (9)	0.0560 (8)	0.0095 (7)	0.0107 (6)	−0.0144 (7)
C1	0.0443 (7)	0.0442 (7)	0.0509 (8)	0.0037 (6)	0.0063 (6)	−0.0076 (6)
C2	0.0576 (9)	0.0474 (8)	0.0535 (9)	0.0092 (7)	0.0107 (7)	0.0012 (7)
C3	0.0576 (9)	0.0457 (8)	0.0676 (11)	0.0115 (7)	0.0123 (8)	−0.0056 (7)
C4	0.0568 (9)	0.0561 (9)	0.0578 (9)	0.0044 (7)	0.0144 (7)	−0.0152 (7)
C5	0.0653 (10)	0.0612 (10)	0.0512 (9)	0.0050 (8)	0.0120 (7)	−0.0006 (8)
C6	0.0584 (9)	0.0467 (8)	0.0567 (9)	0.0107 (7)	0.0083 (7)	0.0008 (7)
C7	0.0500 (8)	0.0475 (8)	0.0536 (9)	0.0098 (6)	0.0062 (6)	−0.0073 (7)
C8	0.0558 (9)	0.0531 (9)	0.0565 (9)	0.0132 (7)	0.0113 (7)	−0.0078 (7)
C9	0.0481 (8)	0.0550 (9)	0.0537 (9)	0.0078 (7)	0.0062 (6)	−0.0136 (7)
C10	0.0439 (7)	0.0546 (9)	0.0518 (8)	0.0040 (6)	0.0048 (6)	−0.0162 (7)
C11	0.0531 (9)	0.0556 (9)	0.0614 (10)	0.0012 (7)	0.0072 (7)	−0.0107 (8)
C12	0.0647 (10)	0.0701 (12)	0.0638 (11)	−0.0064 (9)	0.0113 (8)	−0.0008 (10)
C13	0.0576 (10)	0.0844 (13)	0.0604 (11)	−0.0042 (9)	0.0163 (8)	−0.0137 (10)

Geometric parameters (Å, º) top

Cl—C4	1.7339 (15)	C5—H5	0.98 (2)
O1—C9	1.232 (2)	C6—H6	0.94 (2)
N1—C13	1.338 (3)	C7—C8	1.312 (2)
N1—C10	1.3711 (19)	C7—H7	0.96 (2)
N1—H1	0.83 (2)	C8—C9	1.481 (2)
C1—C6	1.384 (2)	C8—H8	0.96 (2)
C1—C2	1.396 (2)	C9—C10	1.438 (2)
C1—C7	1.465 (2)	C10—C11	1.382 (2)
C2—C3	1.381 (2)	C11—C12	1.388 (3)
C2—H2	0.94 (2)	C11—H11	0.937 (19)
C3—C4	1.370 (3)	C12—C13	1.371 (3)
C3—H3	0.938 (18)	C12—H12	0.95 (2)
C4—C5	1.377 (2)	C13—H13	0.94 (2)
C5—C6	1.380 (2)

C13—N1—C10	109.55 (16)	C8—C7—C1	127.72 (15)
C13—N1—H1	125.3 (15)	C8—C7—H7	118.5 (12)
C10—N1—H1	124.5 (15)	C1—C7—H7	113.7 (12)
C6—C1—C2	118.16 (14)	C7—C8—C9	121.58 (16)
C6—C1—C7	118.54 (14)	C7—C8—H8	120.7 (12)
C2—C1—C7	123.29 (15)	C9—C8—H8	117.7 (12)
C3—C2—C1	120.73 (16)	O1—C9—C10	121.80 (14)
C3—C2—H2	118.7 (12)	O1—C9—C8	121.29 (16)
C1—C2—H2	120.6 (12)	C10—C9—C8	116.91 (14)
C4—C3—C2	119.22 (16)	N1—C10—C11	106.62 (15)
C4—C3—H3	120.2 (11)	N1—C10—C9	121.27 (15)
C2—C3—H3	120.5 (11)	C11—C10—C9	132.10 (14)
C3—C4—C5	121.75 (15)	C10—C11—C12	108.08 (16)
C3—C4—Cl	119.27 (13)	C10—C11—H11	127.2 (12)
C5—C4—Cl	118.98 (14)	C12—C11—H11	124.7 (12)
C4—C5—C6	118.40 (16)	C13—C12—C11	106.80 (18)
C4—C5—H5	121.3 (12)	C13—C12—H12	124.5 (13)
C6—C5—H5	120.3 (12)	C11—C12—H12	128.6 (13)
C5—C6—C1	121.72 (15)	N1—C13—C12	108.94 (17)
C5—C6—H6	119.6 (12)	N1—C13—H13	120.7 (15)
C1—C6—H6	118.7 (12)	C12—C13—H13	130.3 (15)

C6—C1—C2—C3	−0.9 (2)	C7—C8—C9—O1	0.3 (3)
C7—C1—C2—C3	178.38 (16)	C7—C8—C9—C10	−179.47 (15)
C1—C2—C3—C4	−0.3 (3)	C13—N1—C10—C11	−0.09 (19)
C2—C3—C4—C5	1.2 (3)	C13—N1—C10—C9	−179.06 (15)
C2—C3—C4—Cl	−178.39 (13)	O1—C9—C10—N1	0.9 (2)
C3—C4—C5—C6	−1.0 (3)	C8—C9—C10—N1	−179.32 (14)
Cl—C4—C5—C6	178.67 (14)	O1—C9—C10—C11	−177.75 (17)
C4—C5—C6—C1	−0.3 (3)	C8—C9—C10—C11	2.0 (3)
C2—C1—C6—C5	1.2 (3)	N1—C10—C11—C12	−0.27 (19)
C7—C1—C6—C5	−178.12 (15)	C9—C10—C11—C12	178.54 (17)
C6—C1—C7—C8	170.00 (17)	C10—C11—C12—C13	0.5 (2)
C2—C1—C7—C8	−9.3 (3)	C10—N1—C13—C12	0.4 (2)
C1—C7—C8—C9	−177.33 (15)	C11—C12—C13—N1	−0.6 (2)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1···O1ⁱ	0.83 (2)	2.12 (2)	2.902 (2)	156 (2)
C3—H3···CgAⁱⁱ	0.938 (18)	2.897 (17)	3.6339 (19)	136.4 (13)
C6—H6···CgBⁱⁱⁱ	0.94 (2)	2.651 (19)	3.4017 (19)	137.8 (16)

Symmetry codes: (i) −x, −y+1, −z+1; (ii) −x+1, y−1/2, −z+1/2; (iii) x, −y−1/2, z−3/2.

Experimental details

Crystal data
Chemical formula	C₁₃H₁₀ClNO
M_r	231.67
Crystal system, space group	Monoclinic, P2₁/c
Temperature (K)	296
a, b, c (Å)	13.0401 (7), 5.6326 (3), 15.6857 (8)
β (°)	94.979 (3)
V (Å³)	1147.76 (10)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	0.31
Crystal size (mm)	0.30 × 0.22 × 0.20

Data collection
Diffractometer	Bruker KappaAPEXII CCD diffractometer
Absorption correction	Multi-scan (SADABS; Bruker, 2005)
T_min, T_max	0.903, 0.935
No. of measured, independent and observed [I > 2σ(I)] reflections	13745, 3081, 2180
R_int	0.026
(sin θ/λ)_max (Å⁻¹)	0.684

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.043, 0.128, 1.02
No. of reflections	3081
No. of parameters	185
H-atom treatment	All H-atom parameters refined
Δρ_max, Δρ_min (e Å⁻³)	0.29, −0.30

Computer programs: APEX2 (Bruker, 2007), SAINT (Bruker, 2007), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), ORTEP-3 for Windows (Farrugia, 1997) and PLATON (Spek, 2003), WinGX (Farrugia, 1999) and PLATON (Spek, 2003).

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1···O1ⁱ	0.83 (2)	2.12 (2)	2.902 (2)	156 (2)
C3—H3···CgAⁱⁱ	0.938 (18)	2.897 (17)	3.6339 (19)	136.4 (13)
C6—H6···CgBⁱⁱⁱ	0.94 (2)	2.651 (19)	3.4017 (19)	137.8 (16)

Symmetry codes: (i) −x, −y+1, −z+1; (ii) −x+1, y−1/2, −z+1/2; (iii) x, −y−1/2, z−3/2.

Acknowledgements

The authors acknowledge the Higher Education Commision, Islamabad, Pakistan, for funding the purchase of the diffractometer.

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