organic compounds
A triclinic polymorph of methyl (3R,3′S)-1′,1′′-dimethyl-2,2′′-dioxodispiro[indoline-3,2′-pyrrolidine-3′,3′′-indoline]-4′-carboxylate
aDepartment of Physics, S.M.K. Fomra Institute of Technology, Thaiyur, Chennai 603 103, India, bIndustrial Chemistry Laboratory, Central Leather Research Institute, Adyar, Chennai 600 020, India, and cDepartment of Physics, Presidency College (Autonomous), Chennai 600 005, India
*Correspondence e-mail: a_sp59@yahoo.in
In the title compound, C22H21N3O4, the central pyrrolidine ring adopts a C-envelope conformation with a C atom 0.6593 (13) Å displaced from the mean plane formed by the remaining ring atoms. The indoline ring systems (r.m.s. devisations of 0.0356 and 0.0547 Å) are almost perpendicular to the mean plane of the pyrrolidine ring, making dihedral angles of 89.7 (6) and 82.5 (6)°. The acetate group attached to the pyrrolidine ring assumes an extended conformation. In the crystal,N—H⋯O and C—H⋯O hydrogen bonds connect adjacent molecules, forming an infinite tape extending along [1-1-1]. The crystal packing is further consolidated by strong π–π interactions with a centroid–centroid distance of 3.2585 (8) Å. The title compound is a polymorph of previously reported monoclinic structure [Ganesh et al. (2012). Acta Cryst. E68, o2902–o2903].
Related literature
For background literature and the previously reported polymorph, see: Ganesh et al. (2008). For a related structure, see: Wei et al. (2011).
Experimental
Crystal data
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Refinement
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Data collection: APEX2 (Bruker, 2008); cell SAINT (Bruker, 2008); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: ORTEP-3 (Farrugia, 2012); software used to prepare material for publication: SHELXL97 and PLATON (Spek, 2009).
Supporting information
10.1107/S160053681204706X/pv2603sup1.cif
contains datablocks global, I. DOI:Structure factors: contains datablock I. DOI: 10.1107/S160053681204706X/pv2603Isup2.hkl
A mixture of 1 eq of (E)-methyl 2-(1-methyl-2-oxoindolin-3-ylidene) acetate, 1 eq of isatin and 1.5 eq of sarcosine dissolved in acetonitrile was refluxed at 353 K for 8 h. Upon completion of the reaction as determined with the aid of TLC, the reaction mixture was extracted with ethyl acetate and water. The product was dried and purified by
using ethyl acetate and hexane (1:9) as an elutent to afford the title compound in pure form. (Yield = 90%). Single crystals suitable for X-ray diffraction were obtained by slow evaporation of a solution of the title compound in ethyl acetate at room temperature.All H atoms were fixed geometrically and allowed to ride on their parent C atoms, with N—H = 0.86 Å and C—H distances in the range 0.93–0.98 Å with Uiso(H) = 1.5Ueq(methyl C) and 1.2Ueq(non-methyl C/N).
Data collection: APEX2 (Bruker, 2008); cell
SAINT (Bruker, 2008); data reduction: SAINT (Bruker, 2008); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: ORTEP-3 (Farrugia, 2012); software used to prepare material for publication: SHELXL97 (Sheldrick, 2008) and PLATON (Spek, 2009).C22H21N3O4 | Z = 2 |
Mr = 391.42 | F(000) = 412 |
Triclinic, P1 | Dx = 1.319 Mg m−3 |
Hall symbol: -P 1 | Mo Kα radiation, λ = 0.71073 Å |
a = 9.4418 (3) Å | Cell parameters from 8469 reflections |
b = 10.0132 (3) Å | θ = 2.4–34.7° |
c = 12.8861 (4) Å | µ = 0.09 mm−1 |
α = 67.465 (2)° | T = 293 K |
β = 88.237 (2)° | Block, colourless |
γ = 62.842 (1)° | 0.25 × 0.22 × 0.19 mm |
V = 985.68 (5) Å3 |
Bruker APEXII CCD area-detector diffractometer | 8469 independent reflections |
Radiation source: fine-focus sealed tube | 5108 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.028 |
ω and ϕ scans | θmax = 34.7°, θmin = 2.4° |
Absorption correction: multi-scan (SADABS; Bruker, 2008) | h = −15→15 |
Tmin = 0.978, Tmax = 0.983 | k = −16→16 |
23829 measured reflections | l = −20→20 |
Refinement on F2 | Primary atom site location: structure-invariant direct methods |
Least-squares matrix: full | Secondary atom site location: difference Fourier map |
R[F2 > 2σ(F2)] = 0.051 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.158 | H-atom parameters constrained |
S = 1.08 | w = 1/[σ2(Fo2) + (0.0823P)2 + 0.0657P] where P = (Fo2 + 2Fc2)/3 |
8469 reflections | (Δ/σ)max < 0.001 |
265 parameters | Δρmax = 0.29 e Å−3 |
0 restraints | Δρmin = −0.27 e Å−3 |
C22H21N3O4 | γ = 62.842 (1)° |
Mr = 391.42 | V = 985.68 (5) Å3 |
Triclinic, P1 | Z = 2 |
a = 9.4418 (3) Å | Mo Kα radiation |
b = 10.0132 (3) Å | µ = 0.09 mm−1 |
c = 12.8861 (4) Å | T = 293 K |
α = 67.465 (2)° | 0.25 × 0.22 × 0.19 mm |
β = 88.237 (2)° |
Bruker APEXII CCD area-detector diffractometer | 8469 independent reflections |
Absorption correction: multi-scan (SADABS; Bruker, 2008) | 5108 reflections with I > 2σ(I) |
Tmin = 0.978, Tmax = 0.983 | Rint = 0.028 |
23829 measured reflections |
R[F2 > 2σ(F2)] = 0.051 | 0 restraints |
wR(F2) = 0.158 | H-atom parameters constrained |
S = 1.08 | Δρmax = 0.29 e Å−3 |
8469 reflections | Δρmin = −0.27 e Å−3 |
265 parameters |
Geometry. All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds 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 > 2sigma(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. |
x | y | z | Uiso*/Ueq | ||
C1 | 0.7776 (3) | 1.0526 (3) | 0.51871 (15) | 0.0796 (6) | |
H1A | 0.6672 | 1.1089 | 0.5272 | 0.119* | |
H1B | 0.8311 | 1.1134 | 0.5210 | 0.119* | |
H1C | 0.8314 | 0.9442 | 0.5797 | 0.119* | |
C2 | 0.77232 (13) | 0.91697 (13) | 0.39598 (9) | 0.0340 (2) | |
C3 | 0.76315 (11) | 0.95234 (11) | 0.26878 (8) | 0.02661 (19) | |
C4 | 0.76056 (12) | 1.11630 (12) | 0.21751 (10) | 0.0322 (2) | |
C5 | 0.77058 (15) | 1.16217 (15) | 0.30477 (11) | 0.0422 (3) | |
C6 | 0.7641 (2) | 1.3110 (2) | 0.28366 (17) | 0.0670 (5) | |
H6 | 0.7739 | 1.3393 | 0.3429 | 0.080* | |
C7 | 0.7427 (2) | 1.41584 (19) | 0.17152 (19) | 0.0769 (6) | |
H7 | 0.7374 | 1.5172 | 0.1548 | 0.092* | |
C8 | 0.7291 (2) | 1.37485 (16) | 0.08406 (16) | 0.0648 (4) | |
H8 | 0.7136 | 1.4490 | 0.0091 | 0.078* | |
C9 | 0.73808 (15) | 1.22285 (14) | 0.10554 (11) | 0.0443 (3) | |
H9 | 0.7292 | 1.1947 | 0.0461 | 0.053* | |
C10 | 0.61443 (11) | 0.95525 (12) | 0.21822 (9) | 0.0294 (2) | |
H10 | 0.5964 | 0.8689 | 0.2757 | 0.035* | |
C11 | 0.66671 (12) | 0.90746 (15) | 0.11868 (10) | 0.0370 (2) | |
H11A | 0.6483 | 0.8173 | 0.1245 | 0.044* | |
H11B | 0.6070 | 1.0006 | 0.0465 | 0.044* | |
C12 | 0.90212 (11) | 0.81284 (11) | 0.24386 (8) | 0.02558 (18) | |
C13 | 0.93053 (14) | 0.73661 (15) | 0.08136 (10) | 0.0399 (3) | |
H13A | 1.0405 | 0.7158 | 0.0853 | 0.060* | |
H13B | 0.8829 | 0.7789 | 0.0033 | 0.060* | |
H13C | 0.9282 | 0.6357 | 0.1250 | 0.060* | |
C14 | 0.46237 (12) | 1.11772 (13) | 0.18539 (10) | 0.0347 (2) | |
C15 | 0.2897 (3) | 1.3079 (2) | 0.25589 (17) | 0.0936 (7) | |
H15A | 0.3143 | 1.3946 | 0.2131 | 0.140* | |
H15B | 0.2644 | 1.3125 | 0.3276 | 0.140* | |
H15C | 0.1986 | 1.3214 | 0.2135 | 0.140* | |
C16 | 0.92790 (12) | 0.63976 (11) | 0.32962 (8) | 0.0289 (2) | |
C17 | 1.16767 (12) | 0.63888 (13) | 0.34810 (9) | 0.0326 (2) | |
C18 | 1.06891 (11) | 0.79224 (12) | 0.26043 (9) | 0.0299 (2) | |
C19 | 1.13393 (14) | 0.89045 (15) | 0.19952 (12) | 0.0440 (3) | |
H19 | 1.0693 | 0.9923 | 0.1397 | 0.053* | |
C20 | 1.29723 (16) | 0.83568 (18) | 0.22851 (14) | 0.0543 (3) | |
H20 | 1.3422 | 0.9014 | 0.1880 | 0.065* | |
C21 | 1.39322 (15) | 0.68469 (19) | 0.31685 (14) | 0.0547 (4) | |
H21 | 1.5024 | 0.6499 | 0.3353 | 0.066* | |
C22 | 1.32993 (14) | 0.58367 (17) | 0.37874 (12) | 0.0482 (3) | |
H22 | 1.3946 | 0.4822 | 0.4389 | 0.058* | |
N1 | 0.78263 (14) | 1.03949 (13) | 0.41018 (9) | 0.0459 (3) | |
N2 | 0.83966 (10) | 0.85688 (10) | 0.12758 (7) | 0.02941 (18) | |
N3 | 1.08062 (11) | 0.55400 (11) | 0.38933 (8) | 0.0349 (2) | |
H3 | 1.1191 | 0.4587 | 0.4458 | 0.042* | |
O1 | 0.77037 (12) | 0.79974 (10) | 0.47206 (7) | 0.0499 (2) | |
O2 | 0.83142 (10) | 0.58935 (10) | 0.33842 (7) | 0.0409 (2) | |
O3 | 0.38293 (12) | 1.20557 (12) | 0.09240 (8) | 0.0593 (3) | |
O4 | 0.42723 (12) | 1.15085 (11) | 0.27609 (8) | 0.0563 (3) |
U11 | U22 | U33 | U12 | U13 | U23 | |
C1 | 0.1180 (16) | 0.0905 (13) | 0.0559 (10) | −0.0537 (12) | 0.0155 (10) | −0.0508 (10) |
C2 | 0.0382 (5) | 0.0283 (5) | 0.0297 (5) | −0.0120 (4) | 0.0025 (4) | −0.0110 (4) |
C3 | 0.0304 (4) | 0.0215 (4) | 0.0268 (5) | −0.0134 (3) | 0.0023 (3) | −0.0077 (3) |
C4 | 0.0331 (5) | 0.0223 (4) | 0.0400 (6) | −0.0148 (4) | 0.0053 (4) | −0.0098 (4) |
C5 | 0.0475 (6) | 0.0353 (6) | 0.0548 (8) | −0.0246 (5) | 0.0098 (5) | −0.0234 (5) |
C6 | 0.0847 (11) | 0.0541 (8) | 0.0965 (13) | −0.0476 (8) | 0.0291 (9) | −0.0476 (9) |
C7 | 0.0947 (13) | 0.0401 (7) | 0.1167 (16) | −0.0464 (9) | 0.0458 (11) | −0.0374 (9) |
C8 | 0.0760 (10) | 0.0301 (6) | 0.0769 (11) | −0.0284 (7) | 0.0299 (8) | −0.0089 (7) |
C9 | 0.0500 (6) | 0.0282 (5) | 0.0453 (7) | −0.0189 (5) | 0.0117 (5) | −0.0064 (5) |
C10 | 0.0274 (4) | 0.0264 (4) | 0.0334 (5) | −0.0130 (4) | 0.0027 (4) | −0.0112 (4) |
C11 | 0.0291 (4) | 0.0416 (6) | 0.0421 (6) | −0.0132 (4) | −0.0001 (4) | −0.0234 (5) |
C12 | 0.0269 (4) | 0.0216 (4) | 0.0264 (5) | −0.0127 (3) | 0.0022 (3) | −0.0067 (3) |
C13 | 0.0400 (5) | 0.0421 (6) | 0.0370 (6) | −0.0152 (5) | 0.0088 (4) | −0.0216 (5) |
C14 | 0.0307 (5) | 0.0321 (5) | 0.0385 (6) | −0.0134 (4) | 0.0060 (4) | −0.0142 (4) |
C15 | 0.0981 (14) | 0.0496 (9) | 0.0712 (11) | 0.0100 (9) | 0.0338 (10) | −0.0235 (8) |
C16 | 0.0345 (5) | 0.0230 (4) | 0.0280 (5) | −0.0140 (4) | 0.0065 (4) | −0.0093 (4) |
C17 | 0.0308 (4) | 0.0308 (5) | 0.0313 (5) | −0.0122 (4) | 0.0003 (4) | −0.0110 (4) |
C18 | 0.0280 (4) | 0.0275 (4) | 0.0323 (5) | −0.0141 (4) | 0.0019 (4) | −0.0093 (4) |
C19 | 0.0375 (5) | 0.0375 (6) | 0.0529 (7) | −0.0237 (5) | 0.0029 (5) | −0.0075 (5) |
C20 | 0.0395 (6) | 0.0593 (8) | 0.0714 (10) | −0.0340 (6) | 0.0086 (6) | −0.0215 (7) |
C21 | 0.0313 (5) | 0.0623 (8) | 0.0714 (9) | −0.0229 (6) | 0.0003 (6) | −0.0275 (7) |
C22 | 0.0324 (5) | 0.0454 (7) | 0.0511 (7) | −0.0102 (5) | −0.0081 (5) | −0.0143 (6) |
N1 | 0.0614 (6) | 0.0455 (6) | 0.0404 (6) | −0.0272 (5) | 0.0053 (5) | −0.0250 (5) |
N2 | 0.0285 (4) | 0.0307 (4) | 0.0262 (4) | −0.0124 (3) | 0.0022 (3) | −0.0112 (3) |
N3 | 0.0359 (4) | 0.0236 (4) | 0.0309 (5) | −0.0102 (3) | 0.0015 (3) | −0.0025 (3) |
O1 | 0.0732 (6) | 0.0317 (4) | 0.0308 (4) | −0.0189 (4) | 0.0122 (4) | −0.0076 (3) |
O2 | 0.0455 (4) | 0.0325 (4) | 0.0490 (5) | −0.0256 (3) | 0.0095 (4) | −0.0125 (4) |
O3 | 0.0468 (5) | 0.0492 (5) | 0.0499 (6) | 0.0017 (4) | −0.0116 (4) | −0.0191 (5) |
O4 | 0.0584 (6) | 0.0415 (5) | 0.0428 (5) | −0.0039 (4) | 0.0154 (4) | −0.0178 (4) |
C1—N1 | 1.4514 (18) | C12—N2 | 1.4484 (13) |
C1—H1A | 0.9600 | C12—C18 | 1.5028 (13) |
C1—H1B | 0.9600 | C12—C16 | 1.5645 (13) |
C1—H1C | 0.9600 | C13—N2 | 1.4548 (14) |
C2—O1 | 1.2149 (13) | C13—H13A | 0.9600 |
C2—N1 | 1.3529 (15) | C13—H13B | 0.9600 |
C2—C3 | 1.5348 (14) | C13—H13C | 0.9600 |
C3—C4 | 1.5052 (13) | C14—O3 | 1.1904 (14) |
C3—C10 | 1.5497 (13) | C14—O4 | 1.3263 (14) |
C3—C12 | 1.5558 (13) | C15—O4 | 1.4389 (17) |
C4—C9 | 1.3775 (16) | C15—H15A | 0.9600 |
C4—C5 | 1.3879 (17) | C15—H15B | 0.9600 |
C5—C6 | 1.3808 (18) | C15—H15C | 0.9600 |
C5—N1 | 1.4035 (17) | C16—O2 | 1.2112 (12) |
C6—C7 | 1.376 (3) | C16—N3 | 1.3565 (13) |
C6—H6 | 0.9300 | C17—C22 | 1.3803 (15) |
C7—C8 | 1.366 (3) | C17—C18 | 1.3899 (14) |
C7—H7 | 0.9300 | C17—N3 | 1.3946 (14) |
C8—C9 | 1.4003 (18) | C18—C19 | 1.3748 (15) |
C8—H8 | 0.9300 | C19—C20 | 1.3871 (16) |
C9—H9 | 0.9300 | C19—H19 | 0.9300 |
C10—C14 | 1.5048 (14) | C20—C21 | 1.377 (2) |
C10—C11 | 1.5276 (15) | C20—H20 | 0.9300 |
C10—H10 | 0.9800 | C21—C22 | 1.386 (2) |
C11—N2 | 1.4656 (13) | C21—H21 | 0.9300 |
C11—H11A | 0.9700 | C22—H22 | 0.9300 |
C11—H11B | 0.9700 | N3—H3 | 0.8600 |
N1—C1—H1A | 109.5 | C18—C12—C16 | 101.43 (7) |
N1—C1—H1B | 109.5 | C3—C12—C16 | 110.59 (7) |
H1A—C1—H1B | 109.5 | N2—C13—H13A | 109.5 |
N1—C1—H1C | 109.5 | N2—C13—H13B | 109.5 |
H1A—C1—H1C | 109.5 | H13A—C13—H13B | 109.5 |
H1B—C1—H1C | 109.5 | N2—C13—H13C | 109.5 |
O1—C2—N1 | 125.04 (11) | H13A—C13—H13C | 109.5 |
O1—C2—C3 | 126.49 (10) | H13B—C13—H13C | 109.5 |
N1—C2—C3 | 108.47 (9) | O3—C14—O4 | 123.86 (10) |
C4—C3—C2 | 101.98 (8) | O3—C14—C10 | 126.06 (10) |
C4—C3—C10 | 113.45 (8) | O4—C14—C10 | 110.09 (9) |
C2—C3—C10 | 113.21 (8) | O4—C15—H15A | 109.5 |
C4—C3—C12 | 114.98 (8) | O4—C15—H15B | 109.5 |
C2—C3—C12 | 113.55 (8) | H15A—C15—H15B | 109.5 |
C10—C3—C12 | 100.24 (7) | O4—C15—H15C | 109.5 |
C9—C4—C5 | 120.03 (10) | H15A—C15—H15C | 109.5 |
C9—C4—C3 | 131.23 (10) | H15B—C15—H15C | 109.5 |
C5—C4—C3 | 108.51 (10) | O2—C16—N3 | 126.22 (9) |
C6—C5—C4 | 122.02 (14) | O2—C16—C12 | 126.37 (9) |
C6—C5—N1 | 128.08 (13) | N3—C16—C12 | 107.37 (8) |
C4—C5—N1 | 109.88 (10) | C22—C17—C18 | 121.67 (11) |
C7—C6—C5 | 117.35 (15) | C22—C17—N3 | 128.28 (10) |
C7—C6—H6 | 121.3 | C18—C17—N3 | 109.88 (9) |
C5—C6—H6 | 121.3 | C19—C18—C17 | 119.80 (10) |
C8—C7—C6 | 121.67 (13) | C19—C18—C12 | 130.94 (9) |
C8—C7—H7 | 119.2 | C17—C18—C12 | 109.02 (8) |
C6—C7—H7 | 119.2 | C18—C19—C20 | 119.12 (11) |
C7—C8—C9 | 120.99 (15) | C18—C19—H19 | 120.4 |
C7—C8—H8 | 119.5 | C20—C19—H19 | 120.4 |
C9—C8—H8 | 119.5 | C21—C20—C19 | 120.50 (12) |
C4—C9—C8 | 117.92 (14) | C21—C20—H20 | 119.8 |
C4—C9—H9 | 121.0 | C19—C20—H20 | 119.8 |
C8—C9—H9 | 121.0 | C20—C21—C22 | 121.16 (11) |
C14—C10—C11 | 114.04 (9) | C20—C21—H21 | 119.4 |
C14—C10—C3 | 113.06 (8) | C22—C21—H21 | 119.4 |
C11—C10—C3 | 104.49 (8) | C17—C22—C21 | 117.72 (12) |
C14—C10—H10 | 108.3 | C17—C22—H22 | 121.1 |
C11—C10—H10 | 108.3 | C21—C22—H22 | 121.1 |
C3—C10—H10 | 108.3 | C2—N1—C5 | 111.02 (10) |
N2—C11—C10 | 105.43 (8) | C2—N1—C1 | 122.76 (12) |
N2—C11—H11A | 110.7 | C5—N1—C1 | 125.37 (12) |
C10—C11—H11A | 110.7 | C12—N2—C13 | 115.72 (8) |
N2—C11—H11B | 110.7 | C12—N2—C11 | 108.13 (8) |
C10—C11—H11B | 110.7 | C13—N2—C11 | 114.45 (8) |
H11A—C11—H11B | 108.8 | C16—N3—C17 | 111.89 (8) |
N2—C12—C18 | 114.11 (8) | C16—N3—H3 | 124.1 |
N2—C12—C3 | 100.86 (7) | C17—N3—H3 | 124.1 |
C18—C12—C3 | 117.03 (8) | C14—O4—C15 | 116.15 (12) |
N2—C12—C16 | 113.33 (8) | ||
O1—C2—C3—C4 | 176.72 (11) | C18—C12—C16—O2 | −171.33 (10) |
N1—C2—C3—C4 | −3.10 (11) | C3—C12—C16—O2 | 63.84 (13) |
O1—C2—C3—C10 | 54.46 (14) | N2—C12—C16—N3 | 129.09 (9) |
N1—C2—C3—C10 | −125.36 (10) | C18—C12—C16—N3 | 6.33 (10) |
O1—C2—C3—C12 | −58.99 (14) | C3—C12—C16—N3 | −118.50 (9) |
N1—C2—C3—C12 | 121.20 (10) | C22—C17—C18—C19 | 2.17 (18) |
C2—C3—C4—C9 | −173.11 (11) | N3—C17—C18—C19 | −173.57 (10) |
C10—C3—C4—C9 | −51.01 (15) | C22—C17—C18—C12 | 177.20 (10) |
C12—C3—C4—C9 | 63.56 (15) | N3—C17—C18—C12 | 1.46 (12) |
C2—C3—C4—C5 | 1.16 (11) | N2—C12—C18—C19 | 47.46 (15) |
C10—C3—C4—C5 | 123.25 (10) | C3—C12—C18—C19 | −69.93 (15) |
C12—C3—C4—C5 | −122.17 (10) | C16—C12—C18—C19 | 169.68 (12) |
C9—C4—C5—C6 | −2.22 (19) | N2—C12—C18—C17 | −126.83 (9) |
C3—C4—C5—C6 | −177.24 (12) | C3—C12—C18—C17 | 115.78 (10) |
C9—C4—C5—N1 | 176.11 (10) | C16—C12—C18—C17 | −4.61 (11) |
C3—C4—C5—N1 | 1.09 (13) | C17—C18—C19—C20 | −1.35 (19) |
C4—C5—C6—C7 | 1.7 (2) | C12—C18—C19—C20 | −175.14 (12) |
N1—C5—C6—C7 | −176.26 (14) | C18—C19—C20—C21 | 0.2 (2) |
C5—C6—C7—C8 | −0.3 (3) | C19—C20—C21—C22 | 0.1 (2) |
C6—C7—C8—C9 | −0.6 (3) | C18—C17—C22—C21 | −1.76 (19) |
C5—C4—C9—C8 | 1.18 (18) | N3—C17—C22—C21 | 173.13 (12) |
C3—C4—C9—C8 | 174.90 (12) | C20—C21—C22—C17 | 0.6 (2) |
C7—C8—C9—C4 | 0.2 (2) | O1—C2—N1—C5 | −175.84 (11) |
C4—C3—C10—C14 | −33.41 (12) | C3—C2—N1—C5 | 3.98 (13) |
C2—C3—C10—C14 | 82.20 (10) | O1—C2—N1—C1 | −5.9 (2) |
C12—C3—C10—C14 | −156.52 (8) | C3—C2—N1—C1 | 173.94 (13) |
C4—C3—C10—C11 | 91.15 (10) | C6—C5—N1—C2 | 174.92 (14) |
C2—C3—C10—C11 | −153.24 (8) | C4—C5—N1—C2 | −3.28 (15) |
C12—C3—C10—C11 | −31.96 (9) | C6—C5—N1—C1 | 5.3 (2) |
C14—C10—C11—N2 | 132.27 (9) | C4—C5—N1—C1 | −172.92 (14) |
C3—C10—C11—N2 | 8.34 (11) | C18—C12—N2—C13 | 62.19 (11) |
C4—C3—C12—N2 | −77.70 (9) | C3—C12—N2—C13 | −171.46 (8) |
C2—C3—C12—N2 | 165.37 (8) | C16—C12—N2—C13 | −53.25 (11) |
C10—C3—C12—N2 | 44.33 (8) | C18—C12—N2—C11 | −167.94 (8) |
C4—C3—C12—C18 | 46.69 (12) | C3—C12—N2—C11 | −41.58 (9) |
C2—C3—C12—C18 | −70.23 (11) | C16—C12—N2—C11 | 76.63 (10) |
C10—C3—C12—C18 | 168.72 (8) | C10—C11—N2—C12 | 21.22 (11) |
C4—C3—C12—C16 | 162.12 (8) | C10—C11—N2—C13 | 151.79 (9) |
C2—C3—C12—C16 | 45.19 (10) | O2—C16—N3—C17 | 171.68 (10) |
C10—C3—C12—C16 | −75.85 (9) | C12—C16—N3—C17 | −5.99 (11) |
C11—C10—C14—O3 | 1.20 (16) | C22—C17—N3—C16 | −172.33 (12) |
C3—C10—C14—O3 | 120.39 (13) | C18—C17—N3—C16 | 3.04 (12) |
C11—C10—C14—O4 | −178.99 (9) | O3—C14—O4—C15 | −3.9 (2) |
C3—C10—C14—O4 | −59.81 (12) | C10—C14—O4—C15 | 176.33 (15) |
N2—C12—C16—O2 | −48.57 (13) |
D—H···A | D—H | H···A | D···A | D—H···A |
N3—H3···O1i | 0.86 | 2.10 | 2.9107 (12) | 157 |
C15—H15B···O1ii | 0.96 | 2.47 | 3.363 (2) | 155 |
Symmetry codes: (i) −x+2, −y+1, −z+1; (ii) −x+1, −y+2, −z+1. |
Experimental details
Crystal data | |
Chemical formula | C22H21N3O4 |
Mr | 391.42 |
Crystal system, space group | Triclinic, P1 |
Temperature (K) | 293 |
a, b, c (Å) | 9.4418 (3), 10.0132 (3), 12.8861 (4) |
α, β, γ (°) | 67.465 (2), 88.237 (2), 62.842 (1) |
V (Å3) | 985.68 (5) |
Z | 2 |
Radiation type | Mo Kα |
µ (mm−1) | 0.09 |
Crystal size (mm) | 0.25 × 0.22 × 0.19 |
Data collection | |
Diffractometer | Bruker APEXII CCD area-detector diffractometer |
Absorption correction | Multi-scan (SADABS; Bruker, 2008) |
Tmin, Tmax | 0.978, 0.983 |
No. of measured, independent and observed [I > 2σ(I)] reflections | 23829, 8469, 5108 |
Rint | 0.028 |
(sin θ/λ)max (Å−1) | 0.800 |
Refinement | |
R[F2 > 2σ(F2)], wR(F2), S | 0.051, 0.158, 1.08 |
No. of reflections | 8469 |
No. of parameters | 265 |
H-atom treatment | H-atom parameters constrained |
Δρmax, Δρmin (e Å−3) | 0.29, −0.27 |
Computer programs: APEX2 (Bruker, 2008), SAINT (Bruker, 2008), SHELXS97 (Sheldrick, 2008), ORTEP-3 (Farrugia, 2012), SHELXL97 (Sheldrick, 2008) and PLATON (Spek, 2009).
D—H···A | D—H | H···A | D···A | D—H···A |
N3—H3···O1i | 0.86 | 2.10 | 2.9107 (12) | 156.9 |
C15—H15B···O1ii | 0.96 | 2.47 | 3.363 (2) | 154.9 |
Symmetry codes: (i) −x+2, −y+1, −z+1; (ii) −x+1, −y+2, −z+1. |
Acknowledgements
The authors thank Dr Babu Varghese, SAIF, IIT, Chennai, India, for the data collection. ASP thanks the University Grants Commission, India, for a Minor Research Project.
References
Bruker (2008). APEX2, SAINT and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA. Google Scholar
Farrugia, L. J. (2012). J. Appl. Cryst. 45, 849–854. Web of Science CrossRef CAS IUCr Journals Google Scholar
Ganesh, G., Yuvaraj, P. S., Govindan, E., Reddy, B. S. R. & SubbiahPandi, A. (2012). Acta Cryst. E68, o2902–o2903. CSD CrossRef CAS IUCr Journals Google Scholar
Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. Web of Science CrossRef CAS IUCr Journals Google Scholar
Spek, A. L. (2009). Acta Cryst. D65, 148–155. Web of Science CrossRef CAS IUCr Journals Google Scholar
Wei, A. C., Ali, M. A., Choon, T. S., Hemamalini, M. & Fun, H.-K. (2011). Acta Cryst. E67, o3125. Web of Science CSD CrossRef 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.
We have recently reported the structure of the title compound in the monoclinic system (Ganesh et al., 2012). Here we report the structural details of its triclinic polymorph.
The bond lengths and angles in the title molecule (Fig. 1) are within normal ranges and comparable to those reported for its triclinic polymorph (Ganesh et al., 2012) and a closely related structure (Wei et al., 2011). The indoline ring systems (N1/C2-C9 and N3/C12/C16-C22) are individually planar (rmsd's 0.0356 and 0.0547 Å, respectively) and make dihedral angles of 89.69 (6) ° and 82.48 (6)° with respect to the mean plane of the pyrrolidine ring system (N2/C3/C10–C12). The pyrrolidine ring [N2/C3/C10-C12] adopts a C12-envelop conformation with C12 0.6593 (13) Å displaced from the mean-plane formed by the remaining ring atoms. The acetate group assumes an extended conformation (torsion angle C10–C14–O4–C15 = 176.3 (2) °).
The crystal structure is stabilized by intermolecular N3—H3···O1 and C15—H15B···O1 hydrogen bonds. There are strong π–π interactions with a centroid-centroid distance of 3.2585 (8) Å between Cg1 and Cg3 rings. {Cg1 and Cg3 are the centroids of the N1/C2-C5 and N3/C12/C16-C18 rings respectively}.