The title compound, C
19H
17ClN
2O
5, is an important intermediate for the synthesis of the pesticide Indoxacarb [systematic name: (
S)-methyl 7-chloro-2-{[(methoxycarbonyl)[4-(trifluoromethoxy)phenyl]amino]carbonyl}-2
H,3
H,4a
H,5
H-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.
Supporting information
CCDC reference: 995214
Key indicators
- Single-crystal X-ray study
- T = 293 K
- Mean (C-C) = 0.004 Å
- R factor = 0.053
- wR factor = 0.162
- Data-to-parameter ratio = 14.2
checkCIF/PLATON results
No syntax errors found
Alert level A
PLAT015_ALERT_5_A No _shelx_hkl_file record in SHELXL20xy CIF ... Please Do !
Alert level C
PLAT230_ALERT_2_C Hirshfeld Test Diff for N2 -- C10 .. 5.1 su
PLAT241_ALERT_2_C High Ueq as Compared to Neighbors for ..... C11 Check
PLAT241_ALERT_2_C High Ueq as Compared to Neighbors for ..... C16 Check
PLAT242_ALERT_2_C Low Ueq as Compared to Neighbors for ..... C12 Check
PLAT331_ALERT_2_C Small Average Phenyl C-C Dist. C12 -C17 1.37 Ang.
PLAT906_ALERT_3_C Large K value in the Analysis of Variance ...... 2.696 Check
PLAT911_ALERT_3_C Missing # FCF Refl Between THmin & STh/L= 0.600 47 Why ?
Alert level G
PLAT005_ALERT_5_G No _iucr_refine_instructions_details in the CIF Please Do !
PLAT007_ALERT_5_G Number of Unrefined Donor-H Atoms .............. 1 Why ?
PLAT199_ALERT_1_G Reported _cell_measurement_temperature ..... (K) 293 Check
PLAT200_ALERT_1_G Reported _diffrn_ambient_temperature ..... (K) 293 Check
PLAT434_ALERT_2_G Short Inter HL..HL Contact Cl1 .. Cl1 . 3.38 Ang.
PLAT793_ALERT_4_G The Model has Chirality at C8 ............. S Verify
PLAT912_ALERT_4_G Missing # of FCF Reflections Above STh/L= 0.600 2 Note
1 ALERT level A = Most likely a serious problem - resolve or explain
0 ALERT level B = A potentially serious problem, consider carefully
7 ALERT level C = Check. Ensure it is not caused by an omission or oversight
7 ALERT level G = General information/check it is not something unexpected
2 ALERT type 1 CIF construction/syntax error, inconsistent or missing data
6 ALERT type 2 Indicator that the structure model may be wrong or deficient
2 ALERT type 3 Indicator that the structure quality may be low
2 ALERT type 4 Improvement, methodology, query or suggestion
3 ALERT type 5 Informative message, check
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 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).
Methyl 1-[(
Z)-2-(benzyloxycarbonyl)hydrazin-1-ylidene]-5-chloro-2-hydroxyindane-2-carboxylate
top
Crystal data top
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 |
Data collection top
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 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(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) |
Crystal data top
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)° | |
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 = 0.746 | Rint = 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 | Δρmax = 0.35 e Å−3 |
3569 reflections | Δρmin = −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 | 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)* | |
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. |
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)°.