organic compounds\(\def\hfill{\hskip 5em}\def\hfil{\hskip 3em}\def\eqno#1{\hfil {#1}}\)

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ISSN: 2056-9890

Methyl 1-[(Z)-2-(benzyloxycarbonyl)hydrazin-1-yl­idene]-5-chloro-2-hy­droxy­indane-2-carboxylate

aCatalytic Hydrogenation Research Center, Zhejiang University of Technology, Hangzhou, 310014, People's Republic of China
*Correspondence e-mail: wangyifeng@zjut.edu.cn

(Received 13 March 2014; accepted 3 April 2014; online 9 April 2014)

The title compound, C19H17ClN2O5, is an important inter­mediate for the synthesis of the pesticide Indoxacarb [systematic name: (S)-methyl 7-chloro-2-{[(meth­oxy­carbon­yl)[4-(tri­fluoro­meth­oxy)phen­yl]amino]­carbon­yl}-2H,3H,4aH,5H-indeno­[1,2-e][1,3,4]oxadiazine-4a-carboxyl­ate] The C=N double bond has a Z conformation. An intra­molecular N—H⋯O hydrogen bond occurs. In the crystal structure, O—H⋯O hydrogen bonds result in the formation of 12-membered rings lying about inversion centers with R44(12) motifs.

Related literature

For the synthesis of the title compound, see: Annis et al. (1991[Annis, G. D., Barnette, W. E., Mccann, S. F. & Wing, K. D. (1991). PCT Int. Appl. WO, 9211249.]); Annis (1995[Annis, G. D. (1995). PCT Int. Appl. WO, 9529171.]). For graph-set notation, see: Bernstein et al. (1995[Bernstein, J., Davis, R. E., Shimoni, L. & Chang, N.-L. (1995). Angew. Chem. Int. Ed. Engl. 34, 1555-1573.]).

[Scheme 1]

Experimental

Crystal data
  • C19H17ClN2O5

  • Mr = 388.79

  • Triclinic, [P \overline 1]

  • a = 8.362 (3) Å

  • b = 10.627 (3) Å

  • c = 11.470 (4) Å

  • α = 108.575 (6)°

  • β = 99.377 (7)°

  • γ = 100.886 (6)°

  • V = 921.1 (5) Å3

  • Z = 2

  • Mo Kα radiation

  • μ = 0.24 mm−1

  • T = 293 K

  • 0.21 × 0.18 × 0.12 mm

Data collection
  • Bruker SMART CCD area-detector diffractometer

  • Absorption correction: multi-scan (SADABS; Sheldrick, 2000[Sheldrick, G. M. (2000). SADABS. University of Göttingen, Germany.]) Tmin = 0.587, Tmax = 0.746

  • 5494 measured reflections

  • 3569 independent reflections

  • 2965 reflections with I > 2σ(I)

  • Rint = 0.030

Refinement
  • R[F2 > 2σ(F2)] = 0.053

  • wR(F2) = 0.162

  • S = 1.03

  • 3569 reflections

  • 251 parameters

  • H atoms treated by a mixture of independent and constrained refinement

  • Δρmax = 0.35 e Å−3

  • Δρmin = −0.31 e Å−3

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A D—H H⋯A DA D—H⋯A
O1—H1⋯O2i 0.82 2.13 2.890 (2) 154
N2—H2A⋯O1 0.86 (3) 2.37 (2) 2.891 (2) 119.4 (18)
Symmetry code: (i) -x+1, -y, -z+1.

Data collection: SMART (Bruker, 2013[Bruker (2013). SMART and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA.]); cell refinement: SAINT (Bruker, 2013[Bruker (2013). SMART and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA.]); data reduction: SAINT; program(s) used to solve structure: SHELXTL (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); program(s) used to refine structure: SHELXL2013 (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); molecular graphics: SHELXTL; software used to prepare material for publication: SHELXTL.

Supporting information


Comment top

The title compound, which was readily synthesized from the condensation of methyl 5-chloro-1,3-dihydro-2-hydroxy-1-oxo-2H-inden-2-carboxylate and phenylmethyl hydrazinecarboxylate, acts as an intermediate for the synthesis of Indoxacarb. In this article, the crystal structure of the title compound is presented (Fig. 1). The C=N double bond has a Z configuration. The N2—N1—C9—C8 torsion angle is 4.33 (3)°. The crystal structure is stabilized by intermolecular O1—H1···O2 and intramolecular N2—H2A···O1 hydrogen bonds, resulting in the formation of twelve-membered ring lying about an inversion center and representing R44(12) motif. In the crystal, there are weak intermolecular Cl···Cl interactions, with a distance of 3.379 (2) Å. The hydroxyl O atom lies 0.584 (2) Å from the mean plane of the phenyl ring C1···C6. The benzyl C atom lies 0.129 (2) Å from the mean plane of the phenyl ring C12···C17. The dihedral angle of the planes of two phenyl rings is 73.33 (3)°.

Related literature top

For the synthesis of the title compound, see: Annis et al. (1991); Annis (1995). For graph-set notation, see: Bernstein et al. (1995).

Experimental top

In a reaction flask, methyl 5-chloro-1,3-dihydro-2-hydroxy-1-oxo-2H-inden-2- carboxylate (11.20 g, 0.05 mol), phenylmethyl hydrazinecarboxylate (9.13 g, 0.055 mol) and p-toluenesulfonic acid monohydrate (0.95 g, 0.005 mol) were added to toluene (55 ml). The mixture was stirred at 66°C for 8 h. After completion of the reaction (monitored by HPLC), the mixture was cooled to room temperature and filtered. The filter cake was washed with cold methanol (20 ml) and dried at 40°C under vacuum for 4 h, giving a white solid. Single crystals were obtained by slow evaporation of a methanol and dichloromethane solution.

Refinement top

H atoms attached to C and O atoms were placed in calculated positions with O—H = 0.82 Å, C—H = 0.97 (methylene), 0.96 (methyl), 0.93 Å (aromatic H atoms), and Uiso(H) = 1.2Ueq (C, O) in the riding model approximation. The H atom attached to N was located in a difference Fourier map and refined with a distance restraint of N—H = 0.86 (1) Å and Uiso(H) = 1.5Ueq (N).

Computing details top

Data collection: SMART (Bruker, 2013); cell refinement: SAINT (Bruker, 2013); data reduction: SAINT (Bruker, 2013); program(s) used to solve structure: SHELXTL (Sheldrick, 2008); program(s) used to refine structure: SHELXL2013 (Sheldrick, 2008); molecular graphics: SHELXTL (Sheldrick, 2008); software used to prepare material for publication: SHELXTL (Sheldrick, 2008).

Figures top
[Figure 1] Fig. 1. The structure of the title compound. Displacement ellipsoids are drawn at the 50% probability level.
[Figure 2] Fig. 2. The crystal packing of the title compound.
Methyl 1-[(Z)-2-(benzyloxycarbonyl)hydrazin-1-ylidene]-5-chloro-2-hydroxyindane-2-carboxylate top
Crystal data top
C19H17ClN2O5Z = 2
Mr = 388.79F(000) = 404
Triclinic, P1Dx = 1.402 Mg m3
a = 8.362 (3) ÅMo Kα radiation, λ = 0.71073 Å
b = 10.627 (3) ÅCell parameters from 2385 reflections
c = 11.470 (4) Åθ = 2.6–28.1°
α = 108.575 (6)°µ = 0.24 mm1
β = 99.377 (7)°T = 293 K
γ = 100.886 (6)°Prismatic, colorless
V = 921.1 (5) Å30.21 × 0.18 × 0.12 mm
Data collection top
Bruker SMART CCD area-detector
diffractometer
2965 reflections with I > 2σ(I)
ϕ and ω scansRint = 0.030
Absorption correction: multi-scan
(SADABS; Sheldrick, 2000)
θmax = 26.0°, θmin = 1.9°
Tmin = 0.587, Tmax = 0.746h = 910
5494 measured reflectionsk = 1311
3569 independent reflectionsl = 1214
Refinement top
Refinement on F2Hydrogen site location: mixed
Least-squares matrix: fullH atoms treated by a mixture of independent and constrained refinement
R[F2 > 2σ(F2)] = 0.053 w = 1/[σ2(Fo2) + (0.0957P)2 + 0.1511P]
where P = (Fo2 + 2Fc2)/3
wR(F2) = 0.162(Δ/σ)max = 0.001
S = 1.03Δρmax = 0.35 e Å3
3569 reflectionsΔρmin = 0.31 e Å3
251 parametersExtinction correction: SHELXL, Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4
0 restraintsExtinction coefficient: 0.064 (8)
Crystal data top
C19H17ClN2O5γ = 100.886 (6)°
Mr = 388.79V = 921.1 (5) Å3
Triclinic, P1Z = 2
a = 8.362 (3) ÅMo Kα radiation
b = 10.627 (3) ŵ = 0.24 mm1
c = 11.470 (4) ÅT = 293 K
α = 108.575 (6)°0.21 × 0.18 × 0.12 mm
β = 99.377 (7)°
Data collection top
Bruker SMART CCD area-detector
diffractometer
3569 independent reflections
Absorption correction: multi-scan
(SADABS; Sheldrick, 2000)
2965 reflections with I > 2σ(I)
Tmin = 0.587, Tmax = 0.746Rint = 0.030
5494 measured reflections
Refinement top
R[F2 > 2σ(F2)] = 0.0530 restraints
wR(F2) = 0.162H atoms treated by a mixture of independent and constrained refinement
S = 1.03Δρmax = 0.35 e Å3
3569 reflectionsΔρmin = 0.31 e Å3
251 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.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/Ueq
Cl11.28901 (7)0.44224 (8)0.95091 (6)0.0735 (3)
N10.63739 (19)0.07412 (16)0.44508 (14)0.0374 (4)
N20.5019 (2)0.05154 (17)0.34896 (14)0.0402 (4)
O10.41582 (16)0.25433 (16)0.54793 (13)0.0463 (4)
H10.40220.20910.59330.070*
O20.52986 (18)0.16042 (15)0.24204 (13)0.0494 (4)
O30.35071 (19)0.06312 (15)0.15431 (13)0.0510 (4)
O40.4938 (2)0.35295 (19)0.37465 (16)0.0689 (5)
O50.76048 (19)0.43718 (19)0.48013 (16)0.0614 (5)
C10.8288 (2)0.23034 (19)0.63817 (17)0.0361 (4)
C20.9552 (2)0.1639 (2)0.65007 (18)0.0433 (5)
H20.94480.07650.59280.052*
C31.0959 (2)0.2294 (2)0.74786 (19)0.0479 (5)
H31.18220.18700.75770.057*
C41.1070 (2)0.3591 (2)0.83115 (19)0.0475 (5)
C50.9811 (2)0.4255 (2)0.82290 (18)0.0464 (5)
H50.99120.51240.88120.056*
C60.8395 (2)0.3583 (2)0.72483 (17)0.0395 (4)
C70.6855 (2)0.4073 (2)0.69572 (18)0.0448 (5)
H7A0.71590.50030.69640.054*
H7B0.61860.40490.75690.054*
C80.5888 (2)0.3050 (2)0.56156 (17)0.0389 (4)
C90.6780 (2)0.18852 (19)0.53719 (16)0.0354 (4)
C100.4663 (2)0.0664 (2)0.24796 (18)0.0403 (4)
C110.3026 (4)0.1873 (3)0.0421 (2)0.0729 (8)
H11A0.25590.26560.06320.087*
H11B0.40040.20280.01010.087*
C120.1753 (3)0.1721 (2)0.05686 (19)0.0504 (5)
C130.0110 (4)0.1859 (3)0.0493 (2)0.0678 (7)
H130.02000.19740.02160.081*
C140.1088 (3)0.1830 (3)0.1462 (3)0.0735 (8)
H140.21960.19210.14000.088*
C150.0656 (4)0.1668 (3)0.2496 (3)0.0763 (8)
H150.14700.16770.31580.092*
C160.0958 (4)0.1493 (4)0.2567 (3)0.0977 (12)
H160.12620.13460.32680.117*
C170.2163 (3)0.1528 (3)0.1612 (3)0.0761 (8)
H170.32700.14200.16810.091*
C180.6054 (2)0.3681 (2)0.46057 (19)0.0431 (5)
C190.7984 (4)0.5012 (3)0.3910 (3)0.0746 (8)
H19A0.77130.43230.30770.112*
H19B0.91570.54710.41460.112*
H19C0.73350.56680.39140.112*
H2A0.450 (3)0.114 (3)0.351 (2)0.056 (7)*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
Cl10.0416 (4)0.0866 (5)0.0640 (4)0.0131 (3)0.0136 (3)0.0047 (3)
N10.0337 (8)0.0409 (9)0.0366 (8)0.0104 (6)0.0033 (6)0.0145 (7)
N20.0386 (8)0.0400 (9)0.0372 (8)0.0141 (7)0.0008 (7)0.0102 (7)
O10.0338 (7)0.0592 (10)0.0505 (8)0.0171 (6)0.0086 (6)0.0236 (7)
O20.0499 (8)0.0461 (8)0.0480 (8)0.0204 (7)0.0025 (6)0.0112 (6)
O30.0565 (9)0.0446 (8)0.0404 (8)0.0187 (7)0.0073 (6)0.0061 (6)
O40.0599 (10)0.0803 (12)0.0651 (10)0.0054 (9)0.0098 (8)0.0438 (9)
O50.0434 (8)0.0775 (12)0.0759 (11)0.0141 (8)0.0111 (8)0.0468 (10)
C10.0322 (9)0.0411 (10)0.0360 (9)0.0112 (7)0.0069 (7)0.0149 (8)
C20.0407 (10)0.0479 (11)0.0419 (10)0.0191 (9)0.0087 (8)0.0134 (9)
C30.0351 (10)0.0637 (14)0.0478 (11)0.0208 (9)0.0065 (8)0.0211 (10)
C40.0336 (9)0.0597 (13)0.0421 (10)0.0090 (9)0.0007 (8)0.0147 (9)
C50.0411 (10)0.0482 (12)0.0403 (10)0.0110 (9)0.0017 (8)0.0074 (9)
C60.0364 (9)0.0451 (11)0.0369 (9)0.0133 (8)0.0060 (7)0.0147 (8)
C70.0421 (10)0.0462 (11)0.0419 (10)0.0190 (9)0.0021 (8)0.0097 (9)
C80.0335 (9)0.0433 (11)0.0386 (10)0.0139 (8)0.0034 (7)0.0134 (8)
C90.0335 (9)0.0395 (10)0.0351 (9)0.0113 (7)0.0076 (7)0.0154 (8)
C100.0345 (9)0.0444 (11)0.0402 (10)0.0099 (8)0.0049 (7)0.0151 (8)
C110.0904 (19)0.0536 (15)0.0500 (13)0.0273 (14)0.0185 (13)0.0017 (11)
C120.0581 (13)0.0406 (11)0.0401 (11)0.0114 (9)0.0023 (9)0.0059 (9)
C130.0763 (17)0.0797 (18)0.0606 (15)0.0248 (14)0.0260 (13)0.0355 (14)
C140.0481 (13)0.087 (2)0.088 (2)0.0180 (13)0.0125 (13)0.0355 (16)
C150.0760 (18)0.098 (2)0.0528 (14)0.0339 (16)0.0017 (13)0.0258 (14)
C160.093 (2)0.167 (4)0.0721 (19)0.058 (2)0.0336 (17)0.075 (2)
C170.0537 (14)0.109 (2)0.0788 (18)0.0254 (15)0.0204 (13)0.0471 (17)
C180.0434 (10)0.0414 (11)0.0471 (11)0.0174 (8)0.0066 (8)0.0178 (8)
C190.0686 (16)0.0805 (19)0.101 (2)0.0236 (14)0.0298 (15)0.0602 (17)
Geometric parameters (Å, º) top
Cl1—C41.738 (2)C6—C71.505 (3)
N1—C91.272 (2)C7—C81.549 (3)
N1—N21.371 (2)C7—H7A0.9700
N2—C101.350 (3)C7—H7B0.9700
N2—H2A0.86 (3)C8—C181.524 (3)
O1—C81.409 (2)C8—C91.537 (3)
O1—H10.8200C11—C121.495 (3)
O2—C101.206 (2)C11—H11A0.9700
O3—C101.337 (2)C11—H11B0.9700
O3—C111.452 (3)C12—C171.362 (3)
O4—C181.188 (2)C12—C131.374 (4)
O5—C181.308 (3)C13—C141.382 (4)
O5—C191.441 (3)C13—H130.9300
C1—C61.382 (3)C14—C151.346 (4)
C1—C21.390 (2)C14—H140.9300
C1—C91.454 (2)C15—C161.347 (4)
C2—C31.375 (3)C15—H150.9300
C2—H20.9300C16—C171.378 (4)
C3—C41.380 (3)C16—H160.9300
C3—H30.9300C17—H170.9300
C4—C51.381 (3)C19—H19A0.9600
C5—C61.383 (3)C19—H19B0.9600
C5—H50.9300C19—H19C0.9600
C9—N1—N2117.38 (15)N1—C9—C8128.88 (16)
C10—N2—N1116.91 (15)C1—C9—C8108.56 (15)
C10—N2—H2A122.5 (16)O2—C10—O3124.81 (18)
N1—N2—H2A120.2 (16)O2—C10—N2125.41 (17)
C8—O1—H1109.5O3—C10—N2109.77 (16)
C10—O3—C11113.57 (16)O3—C11—C12109.20 (19)
C18—O5—C19117.33 (18)O3—C11—H11A109.8
C6—C1—C2121.31 (17)C12—C11—H11A109.8
C6—C1—C9109.61 (15)O3—C11—H11B109.8
C2—C1—C9128.97 (17)C12—C11—H11B109.8
C3—C2—C1118.98 (18)H11A—C11—H11B108.3
C3—C2—H2120.5C17—C12—C13117.9 (2)
C1—C2—H2120.5C17—C12—C11121.0 (2)
C2—C3—C4118.93 (17)C13—C12—C11121.0 (2)
C2—C3—H3120.5C12—C13—C14120.7 (2)
C4—C3—H3120.5C12—C13—H13119.7
C3—C4—C5123.02 (18)C14—C13—H13119.7
C3—C4—Cl1118.11 (15)C15—C14—C13120.2 (3)
C5—C4—Cl1118.86 (17)C15—C14—H14119.9
C4—C5—C6117.59 (19)C13—C14—H14119.9
C4—C5—H5121.2C14—C15—C16119.8 (2)
C6—C5—H5121.2C14—C15—H15120.1
C1—C6—C5120.12 (17)C16—C15—H15120.1
C1—C6—C7111.90 (16)C15—C16—C17120.6 (3)
C5—C6—C7127.98 (18)C15—C16—H16119.7
C6—C7—C8104.33 (15)C17—C16—H16119.7
C6—C7—H7A110.9C12—C17—C16120.8 (3)
C8—C7—H7A110.9C12—C17—H17119.6
C6—C7—H7B110.9C16—C17—H17119.6
C8—C7—H7B110.9O4—C18—O5125.2 (2)
H7A—C7—H7B108.9O4—C18—C8124.44 (19)
O1—C8—C18106.74 (14)O5—C18—C8110.29 (16)
O1—C8—C9111.28 (16)O5—C19—H19A109.5
C18—C8—C9107.77 (15)O5—C19—H19B109.5
O1—C8—C7114.79 (16)H19A—C19—H19B109.5
C18—C8—C7111.95 (17)O5—C19—H19C109.5
C9—C8—C7104.18 (14)H19A—C19—H19C109.5
N1—C9—C1122.53 (16)H19B—C19—H19C109.5
C9—N1—N2—C10175.94 (17)C7—C8—C9—N1173.21 (19)
C6—C1—C2—C32.2 (3)O1—C8—C9—C1132.92 (15)
C9—C1—C2—C3173.40 (18)C18—C8—C9—C1110.37 (17)
C1—C2—C3—C40.0 (3)C7—C8—C9—C18.7 (2)
C2—C3—C4—C51.6 (3)C11—O3—C10—O21.6 (3)
C2—C3—C4—Cl1177.90 (16)C11—O3—C10—N2179.1 (2)
C3—C4—C5—C61.1 (3)N1—N2—C10—O29.8 (3)
Cl1—C4—C5—C6178.44 (16)N1—N2—C10—O3169.56 (15)
C2—C1—C6—C52.7 (3)C10—O3—C11—C12179.2 (2)
C9—C1—C6—C5173.61 (17)O3—C11—C12—C17107.2 (3)
C2—C1—C6—C7177.73 (18)O3—C11—C12—C1377.1 (3)
C9—C1—C6—C75.9 (2)C17—C12—C13—C141.2 (4)
C4—C5—C6—C11.1 (3)C11—C12—C13—C14174.7 (2)
C4—C5—C6—C7179.5 (2)C12—C13—C14—C150.2 (5)
C1—C6—C7—C811.2 (2)C13—C14—C15—C162.0 (5)
C5—C6—C7—C8168.3 (2)C14—C15—C16—C172.4 (6)
C6—C7—C8—O1133.43 (17)C13—C12—C17—C160.8 (5)
C6—C7—C8—C18104.68 (18)C11—C12—C17—C16175.1 (3)
C6—C7—C8—C911.5 (2)C15—C16—C17—C121.0 (6)
N2—N1—C9—C1173.57 (15)C19—O5—C18—O40.7 (3)
N2—N1—C9—C84.3 (3)C19—O5—C18—C8178.73 (19)
C6—C1—C9—N1179.68 (17)O1—C8—C18—O412.3 (3)
C2—C1—C9—N14.3 (3)C9—C8—C18—O4107.3 (2)
C6—C1—C9—C82.1 (2)C7—C8—C18—O4138.7 (2)
C2—C1—C9—C8173.92 (19)O1—C8—C18—O5169.65 (16)
O1—C8—C9—N149.0 (3)C9—C8—C18—O570.7 (2)
C18—C8—C9—N167.7 (2)C7—C8—C18—O543.3 (2)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
O1—H1···O2i0.822.132.890 (2)154
N2—H2A···O10.86 (3)2.37 (2)2.891 (2)119.4 (18)
Symmetry code: (i) x+1, y, z+1.
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
O1—H1···O2i0.8202.1312.890 (2)153.85
N2—H2A···O10.86 (3)2.37 (2)2.891 (2)119.4 (18)
Symmetry code: (i) x+1, y, z+1.
 

Acknowledgements

We acknowledge the help of Professor Jie Sun of Shanghai Institute of Organic Chemistry.

References

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