organic compounds
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
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 O—H⋯O hydrogen bonds result in the formation of 12-membered rings lying about inversion centers with R44(12) motifs.
CCDC reference: 995214
Related literature
For the synthesis of the title compound, see: Annis et al. (1991); Annis (1995). For graph-set notation, see: Bernstein et al. (1995).
Experimental
Crystal data
|
|
Data collection: SMART (Bruker, 2013); cell SAINT (Bruker, 2013); data reduction: SAINT; program(s) used to solve structure: SHELXTL (Sheldrick, 2008); program(s) used to refine structure: SHELXL2013 (Sheldrick, 2008); molecular graphics: SHELXTL; software used to prepare material for publication: SHELXTL.
Supporting information
CCDC reference: 995214
10.1107/S1600536814007429/pk2520sup1.cif
contains datablock I. DOI:Structure factors: contains datablock I. DOI: 10.1107/S1600536814007429/pk2520Isup2.hkl
Supporting information file. DOI: 10.1107/S1600536814007429/pk2520Isup3.cml
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.
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).
Data collection: SMART (Bruker, 2013); cell
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).Fig. 1. The structure of the title compound. Displacement ellipsoids are drawn at the 50% probability level. | |
Fig. 2. The crystal packing of the title compound. |
C19H17ClN2O5 | Z = 2 |
Mr = 388.79 | F(000) = 404 |
Triclinic, P1 | Dx = 1.402 Mg m−3 |
a = 8.362 (3) Å | Mo Kα radiation, λ = 0.71073 Å |
b = 10.627 (3) Å | Cell parameters from 2385 reflections |
c = 11.470 (4) Å | θ = 2.6–28.1° |
α = 108.575 (6)° | µ = 0.24 mm−1 |
β = 99.377 (7)° | T = 293 K |
γ = 100.886 (6)° | Prismatic, colorless |
V = 921.1 (5) Å3 | 0.21 × 0.18 × 0.12 mm |
Bruker SMART CCD area-detector diffractometer | 2965 reflections with I > 2σ(I) |
ϕ and ω scans | Rint = 0.030 |
Absorption correction: multi-scan (SADABS; Sheldrick, 2000) | θmax = 26.0°, θmin = 1.9° |
Tmin = 0.587, Tmax = 0.746 | h = −9→10 |
5494 measured reflections | k = −13→11 |
3569 independent reflections | l = −12→14 |
Refinement on F2 | Hydrogen site location: mixed |
Least-squares matrix: full | H 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 = 1.03 | Δρmax = 0.35 e Å−3 |
3569 reflections | Δρmin = −0.31 e Å−3 |
251 parameters | Extinction correction: SHELXL, Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4 |
0 restraints | Extinction coefficient: 0.064 (8) |
C19H17ClN2O5 | γ = 100.886 (6)° |
Mr = 388.79 | V = 921.1 (5) Å3 |
Triclinic, P1 | Z = 2 |
a = 8.362 (3) Å | Mo Kα radiation |
b = 10.627 (3) Å | µ = 0.24 mm−1 |
c = 11.470 (4) Å | T = 293 K |
α = 108.575 (6)° | 0.21 × 0.18 × 0.12 mm |
β = 99.377 (7)° |
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 = 0.746 | Rint = 0.030 |
5494 measured reflections |
R[F2 > 2σ(F2)] = 0.053 | 0 restraints |
wR(F2) = 0.162 | H atoms treated by a mixture of independent and constrained refinement |
S = 1.03 | Δρmax = 0.35 e Å−3 |
3569 reflections | Δρmin = −0.31 e Å−3 |
251 parameters |
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. |
x | y | z | Uiso*/Ueq | ||
Cl1 | 1.28901 (7) | 0.44224 (8) | 0.95091 (6) | 0.0735 (3) | |
N1 | 0.63739 (19) | 0.07412 (16) | 0.44508 (14) | 0.0374 (4) | |
N2 | 0.5019 (2) | 0.05154 (17) | 0.34896 (14) | 0.0402 (4) | |
O1 | 0.41582 (16) | 0.25433 (16) | 0.54793 (13) | 0.0463 (4) | |
H1 | 0.4022 | 0.2091 | 0.5933 | 0.070* | |
O2 | 0.52986 (18) | −0.16042 (15) | 0.24204 (13) | 0.0494 (4) | |
O3 | 0.35071 (19) | −0.06312 (15) | 0.15431 (13) | 0.0510 (4) | |
O4 | 0.4938 (2) | 0.35295 (19) | 0.37465 (16) | 0.0689 (5) | |
O5 | 0.76048 (19) | 0.43718 (19) | 0.48013 (16) | 0.0614 (5) | |
C1 | 0.8288 (2) | 0.23034 (19) | 0.63817 (17) | 0.0361 (4) | |
C2 | 0.9552 (2) | 0.1639 (2) | 0.65007 (18) | 0.0433 (5) | |
H2 | 0.9448 | 0.0765 | 0.5928 | 0.052* | |
C3 | 1.0959 (2) | 0.2294 (2) | 0.74786 (19) | 0.0479 (5) | |
H3 | 1.1822 | 0.1870 | 0.7577 | 0.057* | |
C4 | 1.1070 (2) | 0.3591 (2) | 0.83115 (19) | 0.0475 (5) | |
C5 | 0.9811 (2) | 0.4255 (2) | 0.82290 (18) | 0.0464 (5) | |
H5 | 0.9912 | 0.5124 | 0.8812 | 0.056* | |
C6 | 0.8395 (2) | 0.3583 (2) | 0.72483 (17) | 0.0395 (4) | |
C7 | 0.6855 (2) | 0.4073 (2) | 0.69572 (18) | 0.0448 (5) | |
H7A | 0.7159 | 0.5003 | 0.6964 | 0.054* | |
H7B | 0.6186 | 0.4049 | 0.7569 | 0.054* | |
C8 | 0.5888 (2) | 0.3050 (2) | 0.56156 (17) | 0.0389 (4) | |
C9 | 0.6780 (2) | 0.18852 (19) | 0.53719 (16) | 0.0354 (4) | |
C10 | 0.4663 (2) | −0.0664 (2) | 0.24796 (18) | 0.0403 (4) | |
C11 | 0.3026 (4) | −0.1873 (3) | 0.0421 (2) | 0.0729 (8) | |
H11A | 0.2559 | −0.2656 | 0.0632 | 0.087* | |
H11B | 0.4004 | −0.2028 | 0.0101 | 0.087* | |
C12 | 0.1753 (3) | −0.1721 (2) | −0.05686 (19) | 0.0504 (5) | |
C13 | 0.0110 (4) | −0.1859 (3) | −0.0493 (2) | 0.0678 (7) | |
H13 | −0.0200 | −0.1974 | 0.0216 | 0.081* | |
C14 | −0.1088 (3) | −0.1830 (3) | −0.1462 (3) | 0.0735 (8) | |
H14 | −0.2196 | −0.1921 | −0.1400 | 0.088* | |
C15 | −0.0656 (4) | −0.1668 (3) | −0.2496 (3) | 0.0763 (8) | |
H15 | −0.1470 | −0.1677 | −0.3158 | 0.092* | |
C16 | 0.0958 (4) | −0.1493 (4) | −0.2567 (3) | 0.0977 (12) | |
H16 | 0.1262 | −0.1346 | −0.3268 | 0.117* | |
C17 | 0.2163 (3) | −0.1528 (3) | −0.1612 (3) | 0.0761 (8) | |
H17 | 0.3270 | −0.1420 | −0.1681 | 0.091* | |
C18 | 0.6054 (2) | 0.3681 (2) | 0.46057 (19) | 0.0431 (5) | |
C19 | 0.7984 (4) | 0.5012 (3) | 0.3910 (3) | 0.0746 (8) | |
H19A | 0.7713 | 0.4323 | 0.3077 | 0.112* | |
H19B | 0.9157 | 0.5471 | 0.4146 | 0.112* | |
H19C | 0.7335 | 0.5668 | 0.3914 | 0.112* | |
H2A | 0.450 (3) | 0.114 (3) | 0.351 (2) | 0.056 (7)* |
U11 | U22 | U33 | U12 | U13 | U23 | |
Cl1 | 0.0416 (4) | 0.0866 (5) | 0.0640 (4) | 0.0131 (3) | −0.0136 (3) | 0.0047 (3) |
N1 | 0.0337 (8) | 0.0409 (9) | 0.0366 (8) | 0.0104 (6) | 0.0033 (6) | 0.0145 (7) |
N2 | 0.0386 (8) | 0.0400 (9) | 0.0372 (8) | 0.0141 (7) | −0.0008 (7) | 0.0102 (7) |
O1 | 0.0338 (7) | 0.0592 (10) | 0.0505 (8) | 0.0171 (6) | 0.0086 (6) | 0.0236 (7) |
O2 | 0.0499 (8) | 0.0461 (8) | 0.0480 (8) | 0.0204 (7) | 0.0025 (6) | 0.0112 (6) |
O3 | 0.0565 (9) | 0.0446 (8) | 0.0404 (8) | 0.0187 (7) | −0.0073 (6) | 0.0061 (6) |
O4 | 0.0599 (10) | 0.0803 (12) | 0.0651 (10) | 0.0054 (9) | −0.0098 (8) | 0.0438 (9) |
O5 | 0.0434 (8) | 0.0775 (12) | 0.0759 (11) | 0.0141 (8) | 0.0111 (8) | 0.0468 (10) |
C1 | 0.0322 (9) | 0.0411 (10) | 0.0360 (9) | 0.0112 (7) | 0.0069 (7) | 0.0149 (8) |
C2 | 0.0407 (10) | 0.0479 (11) | 0.0419 (10) | 0.0191 (9) | 0.0087 (8) | 0.0134 (9) |
C3 | 0.0351 (10) | 0.0637 (14) | 0.0478 (11) | 0.0208 (9) | 0.0065 (8) | 0.0211 (10) |
C4 | 0.0336 (9) | 0.0597 (13) | 0.0421 (10) | 0.0090 (9) | 0.0007 (8) | 0.0147 (9) |
C5 | 0.0411 (10) | 0.0482 (12) | 0.0403 (10) | 0.0110 (9) | 0.0017 (8) | 0.0074 (9) |
C6 | 0.0364 (9) | 0.0451 (11) | 0.0369 (9) | 0.0133 (8) | 0.0060 (7) | 0.0147 (8) |
C7 | 0.0421 (10) | 0.0462 (11) | 0.0419 (10) | 0.0190 (9) | 0.0021 (8) | 0.0097 (9) |
C8 | 0.0335 (9) | 0.0433 (11) | 0.0386 (10) | 0.0139 (8) | 0.0034 (7) | 0.0134 (8) |
C9 | 0.0335 (9) | 0.0395 (10) | 0.0351 (9) | 0.0113 (7) | 0.0076 (7) | 0.0154 (8) |
C10 | 0.0345 (9) | 0.0444 (11) | 0.0402 (10) | 0.0099 (8) | 0.0049 (7) | 0.0151 (8) |
C11 | 0.0904 (19) | 0.0536 (15) | 0.0500 (13) | 0.0273 (14) | −0.0185 (13) | −0.0017 (11) |
C12 | 0.0581 (13) | 0.0406 (11) | 0.0401 (11) | 0.0114 (9) | −0.0023 (9) | 0.0059 (9) |
C13 | 0.0763 (17) | 0.0797 (18) | 0.0606 (15) | 0.0248 (14) | 0.0260 (13) | 0.0355 (14) |
C14 | 0.0481 (13) | 0.087 (2) | 0.088 (2) | 0.0180 (13) | 0.0125 (13) | 0.0355 (16) |
C15 | 0.0760 (18) | 0.098 (2) | 0.0528 (14) | 0.0339 (16) | −0.0017 (13) | 0.0258 (14) |
C16 | 0.093 (2) | 0.167 (4) | 0.0721 (19) | 0.058 (2) | 0.0336 (17) | 0.075 (2) |
C17 | 0.0537 (14) | 0.109 (2) | 0.0788 (18) | 0.0254 (15) | 0.0204 (13) | 0.0471 (17) |
C18 | 0.0434 (10) | 0.0414 (11) | 0.0471 (11) | 0.0174 (8) | 0.0066 (8) | 0.0178 (8) |
C19 | 0.0686 (16) | 0.0805 (19) | 0.101 (2) | 0.0236 (14) | 0.0298 (15) | 0.0602 (17) |
Cl1—C4 | 1.738 (2) | C6—C7 | 1.505 (3) |
N1—C9 | 1.272 (2) | C7—C8 | 1.549 (3) |
N1—N2 | 1.371 (2) | C7—H7A | 0.9700 |
N2—C10 | 1.350 (3) | C7—H7B | 0.9700 |
N2—H2A | 0.86 (3) | C8—C18 | 1.524 (3) |
O1—C8 | 1.409 (2) | C8—C9 | 1.537 (3) |
O1—H1 | 0.8200 | C11—C12 | 1.495 (3) |
O2—C10 | 1.206 (2) | C11—H11A | 0.9700 |
O3—C10 | 1.337 (2) | C11—H11B | 0.9700 |
O3—C11 | 1.452 (3) | C12—C17 | 1.362 (3) |
O4—C18 | 1.188 (2) | C12—C13 | 1.374 (4) |
O5—C18 | 1.308 (3) | C13—C14 | 1.382 (4) |
O5—C19 | 1.441 (3) | C13—H13 | 0.9300 |
C1—C6 | 1.382 (3) | C14—C15 | 1.346 (4) |
C1—C2 | 1.390 (2) | C14—H14 | 0.9300 |
C1—C9 | 1.454 (2) | C15—C16 | 1.347 (4) |
C2—C3 | 1.375 (3) | C15—H15 | 0.9300 |
C2—H2 | 0.9300 | C16—C17 | 1.378 (4) |
C3—C4 | 1.380 (3) | C16—H16 | 0.9300 |
C3—H3 | 0.9300 | C17—H17 | 0.9300 |
C4—C5 | 1.381 (3) | C19—H19A | 0.9600 |
C5—C6 | 1.383 (3) | C19—H19B | 0.9600 |
C5—H5 | 0.9300 | C19—H19C | 0.9600 |
C9—N1—N2 | 117.38 (15) | N1—C9—C8 | 128.88 (16) |
C10—N2—N1 | 116.91 (15) | C1—C9—C8 | 108.56 (15) |
C10—N2—H2A | 122.5 (16) | O2—C10—O3 | 124.81 (18) |
N1—N2—H2A | 120.2 (16) | O2—C10—N2 | 125.41 (17) |
C8—O1—H1 | 109.5 | O3—C10—N2 | 109.77 (16) |
C10—O3—C11 | 113.57 (16) | O3—C11—C12 | 109.20 (19) |
C18—O5—C19 | 117.33 (18) | O3—C11—H11A | 109.8 |
C6—C1—C2 | 121.31 (17) | C12—C11—H11A | 109.8 |
C6—C1—C9 | 109.61 (15) | O3—C11—H11B | 109.8 |
C2—C1—C9 | 128.97 (17) | C12—C11—H11B | 109.8 |
C3—C2—C1 | 118.98 (18) | H11A—C11—H11B | 108.3 |
C3—C2—H2 | 120.5 | C17—C12—C13 | 117.9 (2) |
C1—C2—H2 | 120.5 | C17—C12—C11 | 121.0 (2) |
C2—C3—C4 | 118.93 (17) | C13—C12—C11 | 121.0 (2) |
C2—C3—H3 | 120.5 | C12—C13—C14 | 120.7 (2) |
C4—C3—H3 | 120.5 | C12—C13—H13 | 119.7 |
C3—C4—C5 | 123.02 (18) | C14—C13—H13 | 119.7 |
C3—C4—Cl1 | 118.11 (15) | C15—C14—C13 | 120.2 (3) |
C5—C4—Cl1 | 118.86 (17) | C15—C14—H14 | 119.9 |
C4—C5—C6 | 117.59 (19) | C13—C14—H14 | 119.9 |
C4—C5—H5 | 121.2 | C14—C15—C16 | 119.8 (2) |
C6—C5—H5 | 121.2 | C14—C15—H15 | 120.1 |
C1—C6—C5 | 120.12 (17) | C16—C15—H15 | 120.1 |
C1—C6—C7 | 111.90 (16) | C15—C16—C17 | 120.6 (3) |
C5—C6—C7 | 127.98 (18) | C15—C16—H16 | 119.7 |
C6—C7—C8 | 104.33 (15) | C17—C16—H16 | 119.7 |
C6—C7—H7A | 110.9 | C12—C17—C16 | 120.8 (3) |
C8—C7—H7A | 110.9 | C12—C17—H17 | 119.6 |
C6—C7—H7B | 110.9 | C16—C17—H17 | 119.6 |
C8—C7—H7B | 110.9 | O4—C18—O5 | 125.2 (2) |
H7A—C7—H7B | 108.9 | O4—C18—C8 | 124.44 (19) |
O1—C8—C18 | 106.74 (14) | O5—C18—C8 | 110.29 (16) |
O1—C8—C9 | 111.28 (16) | O5—C19—H19A | 109.5 |
C18—C8—C9 | 107.77 (15) | O5—C19—H19B | 109.5 |
O1—C8—C7 | 114.79 (16) | H19A—C19—H19B | 109.5 |
C18—C8—C7 | 111.95 (17) | O5—C19—H19C | 109.5 |
C9—C8—C7 | 104.18 (14) | H19A—C19—H19C | 109.5 |
N1—C9—C1 | 122.53 (16) | H19B—C19—H19C | 109.5 |
C9—N1—N2—C10 | 175.94 (17) | C7—C8—C9—N1 | 173.21 (19) |
C6—C1—C2—C3 | −2.2 (3) | O1—C8—C9—C1 | −132.92 (15) |
C9—C1—C2—C3 | 173.40 (18) | C18—C8—C9—C1 | 110.37 (17) |
C1—C2—C3—C4 | 0.0 (3) | C7—C8—C9—C1 | −8.7 (2) |
C2—C3—C4—C5 | 1.6 (3) | C11—O3—C10—O2 | 1.6 (3) |
C2—C3—C4—Cl1 | −177.90 (16) | C11—O3—C10—N2 | −179.1 (2) |
C3—C4—C5—C6 | −1.1 (3) | N1—N2—C10—O2 | 9.8 (3) |
Cl1—C4—C5—C6 | 178.44 (16) | N1—N2—C10—O3 | −169.56 (15) |
C2—C1—C6—C5 | 2.7 (3) | C10—O3—C11—C12 | −179.2 (2) |
C9—C1—C6—C5 | −173.61 (17) | O3—C11—C12—C17 | 107.2 (3) |
C2—C1—C6—C7 | −177.73 (18) | O3—C11—C12—C13 | −77.1 (3) |
C9—C1—C6—C7 | 5.9 (2) | C17—C12—C13—C14 | 1.2 (4) |
C4—C5—C6—C1 | −1.1 (3) | C11—C12—C13—C14 | −174.7 (2) |
C4—C5—C6—C7 | 179.5 (2) | C12—C13—C14—C15 | 0.2 (5) |
C1—C6—C7—C8 | −11.2 (2) | C13—C14—C15—C16 | −2.0 (5) |
C5—C6—C7—C8 | 168.3 (2) | C14—C15—C16—C17 | 2.4 (6) |
C6—C7—C8—O1 | 133.43 (17) | C13—C12—C17—C16 | −0.8 (5) |
C6—C7—C8—C18 | −104.68 (18) | C11—C12—C17—C16 | 175.1 (3) |
C6—C7—C8—C9 | 11.5 (2) | C15—C16—C17—C12 | −1.0 (6) |
N2—N1—C9—C1 | −173.57 (15) | C19—O5—C18—O4 | 0.7 (3) |
N2—N1—C9—C8 | 4.3 (3) | C19—O5—C18—C8 | 178.73 (19) |
C6—C1—C9—N1 | −179.68 (17) | O1—C8—C18—O4 | −12.3 (3) |
C2—C1—C9—N1 | 4.3 (3) | C9—C8—C18—O4 | 107.3 (2) |
C6—C1—C9—C8 | 2.1 (2) | C7—C8—C18—O4 | −138.7 (2) |
C2—C1—C9—C8 | −173.92 (19) | O1—C8—C18—O5 | 169.65 (16) |
O1—C8—C9—N1 | 49.0 (3) | C9—C8—C18—O5 | −70.7 (2) |
C18—C8—C9—N1 | −67.7 (2) | C7—C8—C18—O5 | 43.3 (2) |
D—H···A | D—H | H···A | D···A | 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. |
D—H···A | D—H | H···A | D···A | D—H···A |
O1—H1···O2i | 0.820 | 2.131 | 2.890 (2) | 153.85 |
N2—H2A···O1 | 0.86 (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
Annis, G. D. (1995). PCT Int. Appl. WO, 9529171. Google Scholar
Annis, G. D., Barnette, W. E., Mccann, S. F. & Wing, K. D. (1991). PCT Int. Appl. WO, 9211249. Google Scholar
Bernstein, J., Davis, R. E., Shimoni, L. & Chang, N.-L. (1995). Angew. Chem. Int. Ed. Engl. 34, 1555–1573. CrossRef CAS Web of Science Google Scholar
Bruker (2013). SMART and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA. Google Scholar
Sheldrick, G. M. (2000). SADABS. University of Göttingen, Germany. Google Scholar
Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. Web of Science CrossRef CAS IUCr Journals Google Scholar
This is an open-access article distributed under the terms of the Creative Commons Attribution (CC-BY) Licence, which permits unrestricted use, distribution, and reproduction in any medium, provided the original authors and source are cited.
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)°.