N-Benzoyl-N-(3-methyl­phen­yl)-O-[2-(2-nitro­phen­yl)acet­yl]hydroxyl­amine

Zhang, K.; He, D.

doi:10.1107/S1600536811025864

organic compounds

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ISSN: 2056-9890

Volume 67| Part 8| August 2011| Page o1966

doi:10.1107/S1600536811025864

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N-Benzoyl-N-(3-methylphenyl)-O-[2-(2-nitrophenyl)acetyl]hydroxylamine

Kai Zhang ^a and Dian He ^a ^*

^aInstitute of Medicinal Chemistry School of Pharmacy, Lanzhou University, Lanzhou 730000, Gansu Province, People's Republic of China
^*Correspondence e-mail: hed@lzu.edu.cn

(Received 5 May 2011; accepted 30 June 2011; online 9 July 2011)

In the title molecule, C₂₂H₁₈N₂O₅, the nitro-substituted ring makes a dihedral angle of 81.9 (1)° with the benzoyl ring and a dihedral angle of 12.1 (1)° with the methyl-substituted ring.

Related literature

For applications, see: Zeng et al. (2003 ). For the preparation, see: Ayyangark et al. (1986 ).

Experimental

Crystal data

C₂₂H₁₈N₂O₅
M_r = 390.38
Monoclinic, P 2₁ /c
a = 16.34 (2) Å
b = 8.459 (10) Å
c = 14.862 (18) Å
β = 109.869 (11)°
V = 1932 (4) Å³
Z = 4
Mo Kα radiation
μ = 0.10 mm⁻¹
T = 296 K
0.25 × 0.24 × 0.21 mm

Data collection

Bruker APEXII CCD diffractometer
Absorption correction: multi-scan (SADABS; Sheldrick, 1996 ) T_min = 0.976, T_max = 0.980
10929 measured reflections
3591 independent reflections
2242 reflections with I > 2σ(I)
R_int = 0.047

Refinement

R[F² > 2σ(F²)] = 0.050
wR(F²) = 0.123
S = 1.00
3591 reflections
263 parameters
H-atom parameters constrained
Δρ_max = 0.18 e Å⁻³
Δρ_min = −0.21 e Å⁻³

Data collection: APEX2 (Bruker, 2009 ) ; cell refinement: SAINT (Bruker, 2009); 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: SHELXL97.

Supporting information

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536811025864/ld2012sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536811025864/ld2012Isup2.hkl

Supporting information file. DOI: 10.1107/S1600536811025864/ld2012Isup3.cml

checkCIF report

Comment top

Hydroxamic acid derivatives have received considerable attention in recent years as the result of the discovery of their role in the biochemical toxicology of many drugs and other chemicals. Thus, these compounds continue to attract much attention as potential biological agents. The title molecule, C₂₂H₁₈N₂O₅, contains three branched chains with its centre placed at midpoint of the N. The phenyl ring C1—C6 makes a dihedral angle of 81.85 (8)° with the phenyl ring C10—C15 of benzoyl group, and 12.08 (8)° with the penyl ring C16—C21.

Related literature top

For related literature [on what subject?], see: Zeng et al. (2003). For the preparation, see: Ayyangark et al. (1986).

Experimental top

The title compound, C₂₂H₁₈N₂O₅ was prepared according to the method described by Ayyangark et al. (1986). Crystals of (I) suitable for single-crystal X-ray analysis were grown by slow evaporation of a solution in dichloromethane-methanol (1:3 v/v).

Computing details top

Data collection: APEX2 (Bruker, 2009); cell refinement: SAINT (Bruker, 2009); data reduction: SAINT (Bruker, 2009); 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: SHELXL97 (Sheldrick, 2008).

Figures top

Fig. 1. The molecular structure of the title compound with the atomic numbering and 50% probability displacement dllipsoids. H atoms are shown as small spheres of arbitrary radius.

N-Benzoyl-N-(3-methylphenyl)-O-[2-(2- nitrophenyl)acetyl]hydroxylamine top

Crystal data top

C₂₂H₁₈N₂O₅	F(000) = 816
M_r = 390.38	D_x = 1.342 Mg m⁻³
Monoclinic, P2₁/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 2435 reflections
a = 16.34 (2) Å	θ = 2.7–22.3°
b = 8.459 (10) Å	µ = 0.10 mm⁻¹
c = 14.862 (18) Å	T = 296 K
β = 109.869 (11)°	Block, yellow
V = 1932 (4) Å³	0.25 × 0.24 × 0.21 mm
Z = 4

Data collection top

Bruker APEXII CCD diffractometer	3591 independent reflections
Radiation source: fine-focus sealed tube	2242 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.047
ϕ and ω scans	θ_max = 25.5°, θ_min = 2.7°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	h = −19→15
T_min = 0.976, T_max = 0.980	k = −10→10
10929 measured reflections	l = −18→18

Refinement top

Refinement on F²	0 restraints
Least-squares matrix: full	H-atom parameters constrained
R[F² > 2σ(F²)] = 0.050	w = 1/[σ²(F_o²) + (0.0508P)² + 0.3323P] where P = (F_o² + 2F_c²)/3
wR(F²) = 0.123	(Δ/σ)_max < 0.001
S = 1.00	Δρ_max = 0.18 e Å⁻³
3591 reflections	Δρ_min = −0.21 e Å⁻³
263 parameters

Crystal data top

C₂₂H₁₈N₂O₅	V = 1932 (4) Å³
M_r = 390.38	Z = 4
Monoclinic, P2₁/c	Mo Kα radiation
a = 16.34 (2) Å	µ = 0.10 mm⁻¹
b = 8.459 (10) Å	T = 296 K
c = 14.862 (18) Å	0.25 × 0.24 × 0.21 mm
β = 109.869 (11)°

Data collection top

Bruker APEXII CCD diffractometer	3591 independent reflections
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	2242 reflections with I > 2σ(I)
T_min = 0.976, T_max = 0.980	R_int = 0.047
10929 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.050	0 restraints
wR(F²) = 0.123	H-atom parameters constrained
S = 1.00	Δρ_max = 0.18 e Å⁻³
3591 reflections	Δρ_min = −0.21 e Å⁻³
263 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
C1	0.09639 (15)	0.0309 (3)	1.13097 (16)	0.0513 (6)
C2	0.01484 (17)	−0.0114 (4)	1.13187 (18)	0.0696 (8)
H2	−0.0264	0.0653	1.1303	0.084*
C3	−0.0036 (2)	−0.1670 (5)	1.1352 (2)	0.0857 (10)
H3	−0.0583	−0.1977	1.1349	0.103*
C4	0.0570 (2)	−0.2781 (4)	1.1388 (2)	0.0910 (10)
H4	0.0439	−0.3846	1.1412	0.109*
C5	0.13830 (19)	−0.2336 (3)	1.13877 (19)	0.0710 (8)
H5	0.1792	−0.3114	1.1414	0.085*
C6	0.16037 (15)	−0.0779 (3)	1.13499 (15)	0.0495 (6)
C7	0.25040 (15)	−0.0379 (3)	1.13676 (16)	0.0527 (6)
H7A	0.2704	0.0563	1.1752	0.063*
H7B	0.2895	−0.1237	1.1668	0.063*
C8	0.25400 (15)	−0.0102 (3)	1.03894 (17)	0.0431 (5)
C9	0.38632 (13)	−0.0232 (3)	0.93782 (15)	0.0375 (5)
C10	0.39160 (13)	−0.0260 (2)	0.83950 (14)	0.0357 (5)
C11	0.32888 (15)	0.0383 (3)	0.76029 (15)	0.0481 (6)
H11	0.2829	0.0956	0.7674	0.058*
C12	0.33474 (18)	0.0170 (3)	0.67094 (16)	0.0620 (7)
H12	0.2928	0.0610	0.6178	0.074*
C13	0.40156 (19)	−0.0683 (3)	0.65957 (18)	0.0655 (8)
H13	0.4049	−0.0825	0.5988	0.079*
C14	0.46365 (18)	−0.1331 (3)	0.73773 (19)	0.0641 (7)
H14	0.5092	−0.1912	0.7302	0.077*
C15	0.45842 (15)	−0.1119 (3)	0.82721 (16)	0.0485 (6)
H15	0.5006	−0.1562	0.8801	0.058*
C16	0.32922 (14)	0.2572 (2)	0.92940 (13)	0.0374 (5)
C17	0.25051 (15)	0.3294 (3)	0.91822 (15)	0.0440 (5)
H17	0.2056	0.2701	0.9264	0.053*
C18	0.23706 (15)	0.4868 (3)	0.89531 (15)	0.0452 (6)
C19	0.30418 (17)	0.5693 (3)	0.88050 (16)	0.0521 (6)
H19	0.2965	0.6755	0.8634	0.063*
C20	0.38237 (16)	0.4971 (3)	0.89061 (16)	0.0531 (6)
H20	0.4264	0.5551	0.8797	0.064*
C21	0.39630 (15)	0.3411 (3)	0.91646 (15)	0.0442 (6)
H21	0.4497	0.2935	0.9250	0.053*
C22	0.15279 (17)	0.5646 (3)	0.8891 (2)	0.0673 (7)
H22A	0.1062	0.5181	0.8377	0.101*
H22B	0.1560	0.6756	0.8772	0.101*
H22C	0.1422	0.5498	0.9482	0.101*
N1	0.33979 (12)	0.0969 (2)	0.95831 (12)	0.0430 (5)
N2	0.11232 (16)	0.1993 (3)	1.12655 (17)	0.0713 (6)
O1	0.20433 (11)	−0.0556 (2)	0.96539 (12)	0.0599 (5)
O2	0.32692 (9)	0.07666 (17)	1.04773 (9)	0.0445 (4)
O3	0.41541 (10)	−0.12978 (17)	0.99348 (10)	0.0489 (4)
O4	0.16263 (14)	0.2435 (2)	1.08809 (14)	0.0828 (6)
O5	0.0756 (2)	0.2889 (3)	1.1631 (2)	0.1459 (12)

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
C1	0.0461 (15)	0.0671 (17)	0.0454 (14)	−0.0063 (13)	0.0217 (12)	0.0015 (12)
C2	0.0453 (16)	0.102 (2)	0.0651 (18)	−0.0020 (16)	0.0237 (13)	0.0064 (16)
C3	0.053 (2)	0.121 (3)	0.086 (2)	−0.034 (2)	0.0293 (17)	0.001 (2)
C4	0.088 (3)	0.087 (3)	0.106 (3)	−0.032 (2)	0.043 (2)	0.0033 (19)
C5	0.073 (2)	0.0679 (19)	0.084 (2)	−0.0031 (16)	0.0420 (17)	0.0096 (15)
C6	0.0469 (15)	0.0653 (17)	0.0411 (13)	−0.0061 (13)	0.0213 (11)	0.0053 (11)
C7	0.0464 (14)	0.0754 (17)	0.0431 (13)	0.0019 (13)	0.0239 (12)	0.0127 (12)
C8	0.0396 (13)	0.0489 (14)	0.0464 (14)	−0.0004 (11)	0.0218 (12)	0.0058 (11)
C9	0.0327 (12)	0.0396 (12)	0.0414 (12)	−0.0078 (10)	0.0144 (10)	−0.0002 (10)
C10	0.0359 (12)	0.0376 (12)	0.0356 (11)	−0.0061 (10)	0.0149 (10)	0.0008 (10)
C11	0.0468 (14)	0.0554 (15)	0.0425 (13)	0.0050 (11)	0.0158 (12)	0.0007 (11)
C12	0.0725 (18)	0.0729 (18)	0.0371 (14)	0.0067 (15)	0.0140 (13)	0.0031 (12)
C13	0.0731 (19)	0.087 (2)	0.0455 (15)	0.0037 (16)	0.0315 (15)	−0.0020 (14)
C14	0.0576 (17)	0.085 (2)	0.0607 (17)	0.0100 (15)	0.0339 (15)	−0.0015 (15)
C15	0.0443 (14)	0.0586 (15)	0.0444 (13)	0.0007 (12)	0.0175 (11)	0.0007 (11)
C16	0.0426 (13)	0.0394 (12)	0.0330 (11)	−0.0025 (10)	0.0166 (10)	−0.0013 (9)
C17	0.0413 (14)	0.0485 (14)	0.0446 (13)	−0.0065 (11)	0.0177 (11)	−0.0041 (11)
C18	0.0514 (14)	0.0436 (14)	0.0395 (13)	0.0020 (12)	0.0140 (11)	−0.0055 (10)
C19	0.0669 (18)	0.0396 (13)	0.0460 (14)	−0.0043 (13)	0.0141 (13)	−0.0030 (11)
C20	0.0577 (16)	0.0493 (15)	0.0561 (15)	−0.0172 (13)	0.0241 (12)	−0.0019 (12)
C21	0.0407 (13)	0.0516 (14)	0.0432 (13)	−0.0041 (11)	0.0182 (11)	−0.0022 (11)
C22	0.0662 (18)	0.0581 (17)	0.0765 (19)	0.0138 (14)	0.0229 (15)	−0.0032 (14)
N1	0.0497 (11)	0.0489 (12)	0.0410 (10)	0.0054 (9)	0.0291 (9)	0.0080 (9)
N2	0.0727 (16)	0.0707 (17)	0.0808 (17)	0.0045 (14)	0.0397 (14)	−0.0011 (13)
O1	0.0552 (11)	0.0786 (13)	0.0482 (10)	−0.0193 (9)	0.0205 (9)	−0.0073 (9)
O2	0.0425 (9)	0.0603 (10)	0.0370 (8)	−0.0055 (8)	0.0217 (7)	0.0027 (7)
O3	0.0581 (11)	0.0457 (10)	0.0421 (9)	0.0055 (8)	0.0159 (8)	0.0084 (8)
O4	0.0943 (15)	0.0726 (13)	0.0992 (15)	−0.0161 (12)	0.0560 (13)	0.0011 (11)
O5	0.182 (3)	0.0902 (19)	0.224 (3)	0.0186 (18)	0.144 (3)	−0.0170 (19)

Geometric parameters (Å, º) top

C1—C6	1.379 (3)	C12—H12	0.9300
C1—C2	1.385 (4)	C13—C14	1.370 (4)
C1—N2	1.453 (4)	C13—H13	0.9300
C2—C3	1.355 (5)	C14—C15	1.373 (3)
C2—H2	0.9300	C14—H14	0.9300
C3—C4	1.353 (5)	C15—H15	0.9300
C3—H3	0.9300	C16—C21	1.373 (3)
C4—C5	1.380 (4)	C16—C17	1.382 (3)
C4—H4	0.9300	C16—N1	1.415 (3)
C5—C6	1.372 (4)	C17—C18	1.373 (3)
C5—H5	0.9300	C17—H17	0.9300
C6—C7	1.501 (3)	C18—C19	1.380 (3)
C7—C8	1.493 (3)	C18—C22	1.500 (4)
C7—H7A	0.9700	C19—C20	1.378 (3)
C7—H7B	0.9700	C19—H19	0.9300
C8—O1	1.182 (3)	C20—C21	1.371 (3)
C8—O2	1.368 (3)	C20—H20	0.9300
C9—O3	1.206 (3)	C21—H21	0.9300
C9—N1	1.365 (3)	C22—H22A	0.9600
C9—C10	1.493 (3)	C22—H22B	0.9600
C10—C15	1.375 (3)	C22—H22C	0.9600
C10—C11	1.383 (3)	N1—O2	1.425 (2)
C11—C12	1.375 (3)	N2—O5	1.205 (3)
C11—H11	0.9300	N2—O4	1.209 (3)
C12—C13	1.367 (4)

C6—C1—C2	123.0 (3)	C12—C13—H13	120.0
C6—C1—N2	120.8 (2)	C14—C13—H13	120.0
C2—C1—N2	116.2 (2)	C13—C14—C15	119.8 (2)
C3—C2—C1	118.6 (3)	C13—C14—H14	120.1
C3—C2—H2	120.7	C15—C14—H14	120.1
C1—C2—H2	120.7	C10—C15—C14	120.7 (2)
C2—C3—C4	120.5 (3)	C10—C15—H15	119.6
C2—C3—H3	119.8	C14—C15—H15	119.6
C4—C3—H3	119.8	C21—C16—C17	120.6 (2)
C3—C4—C5	120.2 (3)	C21—C16—N1	121.1 (2)
C3—C4—H4	119.9	C17—C16—N1	118.19 (19)
C5—C4—H4	119.9	C18—C17—C16	121.5 (2)
C6—C5—C4	121.9 (3)	C18—C17—H17	119.3
C6—C5—H5	119.1	C16—C17—H17	119.3
C4—C5—H5	119.1	C17—C18—C19	117.5 (2)
C5—C6—C1	115.9 (2)	C17—C18—C22	120.4 (2)
C5—C6—C7	119.1 (2)	C19—C18—C22	122.1 (2)
C1—C6—C7	125.0 (2)	C18—C19—C20	121.1 (2)
C8—C7—C6	112.39 (19)	C18—C19—H19	119.4
C8—C7—H7A	109.1	C20—C19—H19	119.4
C6—C7—H7A	109.1	C21—C20—C19	121.1 (2)
C8—C7—H7B	109.1	C21—C20—H20	119.4
C6—C7—H7B	109.1	C19—C20—H20	119.4
H7A—C7—H7B	107.9	C20—C21—C16	118.2 (2)
O1—C8—O2	124.4 (2)	C20—C21—H21	120.9
O1—C8—C7	127.4 (2)	C16—C21—H21	120.9
O2—C8—C7	108.21 (19)	C18—C22—H22A	109.5
O3—C9—N1	121.6 (2)	C18—C22—H22B	109.5
O3—C9—C10	121.3 (2)	H22A—C22—H22B	109.5
N1—C9—C10	116.88 (19)	C18—C22—H22C	109.5
C15—C10—C11	119.2 (2)	H22A—C22—H22C	109.5
C15—C10—C9	116.82 (19)	H22B—C22—H22C	109.5
C11—C10—C9	123.7 (2)	C9—N1—C16	131.76 (17)
C12—C11—C10	119.7 (2)	C9—N1—O2	112.86 (16)
C12—C11—H11	120.1	C16—N1—O2	110.92 (15)
C10—C11—H11	120.1	O5—N2—O4	122.8 (3)
C13—C12—C11	120.6 (2)	O5—N2—C1	118.2 (2)
C13—C12—H12	119.7	O4—N2—C1	119.1 (2)
C11—C12—H12	119.7	C8—O2—N1	112.06 (16)
C12—C13—C14	119.9 (2)

C6—C1—C2—C3	−1.2 (4)	C21—C16—C17—C18	−0.9 (3)
N2—C1—C2—C3	179.5 (2)	N1—C16—C17—C18	176.48 (19)
C1—C2—C3—C4	0.9 (4)	C16—C17—C18—C19	2.2 (3)
C2—C3—C4—C5	−0.2 (5)	C16—C17—C18—C22	−176.5 (2)
C3—C4—C5—C6	−0.1 (5)	C17—C18—C19—C20	−1.5 (3)
C4—C5—C6—C1	−0.2 (4)	C22—C18—C19—C20	177.2 (2)
C4—C5—C6—C7	179.1 (2)	C18—C19—C20—C21	−0.5 (3)
C2—C1—C6—C5	0.8 (3)	C19—C20—C21—C16	1.8 (3)
N2—C1—C6—C5	−179.9 (2)	C17—C16—C21—C20	−1.1 (3)
C2—C1—C6—C7	−178.3 (2)	N1—C16—C21—C20	−178.47 (19)
N2—C1—C6—C7	1.0 (3)	O3—C9—N1—C16	150.7 (2)
C5—C6—C7—C8	97.3 (3)	C10—C9—N1—C16	−35.5 (3)
C1—C6—C7—C8	−83.5 (3)	O3—C9—N1—O2	−2.9 (3)
C6—C7—C8—O1	−21.8 (4)	C10—C9—N1—O2	170.82 (16)
C6—C7—C8—O2	159.1 (2)	C21—C16—N1—C9	−35.1 (3)
O3—C9—C10—C15	−26.3 (3)	C17—C16—N1—C9	147.5 (2)
N1—C9—C10—C15	159.93 (19)	C21—C16—N1—O2	118.89 (19)
O3—C9—C10—C11	146.8 (2)	C17—C16—N1—O2	−58.5 (2)
N1—C9—C10—C11	−26.9 (3)	C6—C1—N2—O5	−148.5 (3)
C15—C10—C11—C12	−0.7 (3)	C2—C1—N2—O5	30.9 (4)
C9—C10—C11—C12	−173.7 (2)	C6—C1—N2—O4	30.3 (4)
C10—C11—C12—C13	0.6 (4)	C2—C1—N2—O4	−150.3 (2)
C11—C12—C13—C14	−0.2 (4)	O1—C8—O2—N1	−4.2 (3)
C12—C13—C14—C15	0.0 (4)	C7—C8—O2—N1	174.84 (16)
C11—C10—C15—C14	0.5 (3)	C9—N1—O2—C8	−87.7 (2)
C9—C10—C15—C14	174.0 (2)	C16—N1—O2—C8	113.1 (2)
C13—C14—C15—C10	−0.2 (4)

Experimental details

Crystal data
Chemical formula	C₂₂H₁₈N₂O₅
M_r	390.38
Crystal system, space group	Monoclinic, P2₁/c
Temperature (K)	296
a, b, c (Å)	16.34 (2), 8.459 (10), 14.862 (18)
β (°)	109.869 (11)
V (Å³)	1932 (4)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	0.10
Crystal size (mm)	0.25 × 0.24 × 0.21

Data collection
Diffractometer	Bruker APEXII CCD diffractometer
Absorption correction	Multi-scan (SADABS; Sheldrick, 1996)
T_min, T_max	0.976, 0.980
No. of measured, independent and observed [I > 2σ(I)] reflections	10929, 3591, 2242
R_int	0.047
(sin θ/λ)_max (Å⁻¹)	0.606

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.050, 0.123, 1.00
No. of reflections	3591
No. of parameters	263
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.18, −0.21

Computer programs: APEX2 (Bruker, 2009), SAINT (Bruker, 2009), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), SHELXTL (Sheldrick, 2008).

Acknowledgements

This work was supported by the Fundamental Research Funds for the Central Universities (lzujbky-2010–137).

References

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