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

Dong, K.; Wang, Y.

doi:10.1107/S1600536814007429

organic compounds

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ISSN: 2056-9890

Volume 70| Part 5| May 2014| Page o527

doi:10.1107/S1600536814007429

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

Kun Dong ^a and Yifeng Wang ^a ^*

^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.

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

C₁₉H₁₇ClN₂O₅
M_r = 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 ) T_min = 0.587, T_max = 0.746
5494 measured reflections
3569 independent reflections
2965 reflections with I > 2σ(I)
R_int = 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
Δρ_max = 0.35 e Å⁻³
Δρ_min = −0.31 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

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.

Data collection: SMART (Bruker, 2013 ); cell refinement: 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

Crystal structure: contains datablock I. DOI: 10.1107/S1600536814007429/pk2520sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536814007429/pk2520Isup2.hkl

Supporting information file. DOI: 10.1107/S1600536814007429/pk2520Isup3.cml

checkCIF report

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.

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

	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.

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

Crystal data top

C₁₉H₁₇ClN₂O₅	Z = 2
M_r = 388.79	F(000) = 404
Triclinic, P1	D_x = 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

Data collection top

Bruker SMART CCD area-detector diffractometer	2965 reflections with I > 2σ(I)
ϕ and ω scans	R_int = 0.030
Absorption correction: multi-scan (SADABS; Sheldrick, 2000)	θ_max = 26.0°, θ_min = 1.9°
T_min = 0.587, T_max = 0.746	h = −9→10
5494 measured reflections	k = −13→11
3569 independent reflections	l = −12→14

Refinement top

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(F_o²) + (0.0957P)² + 0.1511P] where P = (F_o² + 2F_c²)/3
wR(F²) = 0.162	(Δ/σ)_max = 0.001
S = 1.03	Δρ_max = 0.35 e Å⁻³
3569 reflections	Δρ_min = −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)

Crystal data top

C₁₉H₁₇ClN₂O₅	γ = 100.886 (6)°
M_r = 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)°

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)
T_min = 0.587, T_max = 0.746	R_int = 0.030
5494 measured reflections

Refinement top

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	Δρ_max = 0.35 e Å⁻³
3569 reflections	Δρ_min = −0.31 e Å⁻³
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

	x	y	z	U_iso*/U_eq
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)*

Atomic displacement parameters (Å²) top

	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)

Geometric parameters (Å, º) top

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)

Hydrogen-bond geometry (Å, º) top

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.

Hydrogen-bond geometry (Å, º) top

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

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

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

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Experimental

Crystal data

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Refinement

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organic compounds

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