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In the title compound, C
19H
19N
3O
3, the oxindole residue and the 4-methylphenyl ring are almost perpendicular to the pyrrolidine ring. The pyrrolidine ring adopts an envelope conformation. The molecular packing is stabilized by N—H
O hydrogen bonds and C—H
O interactions, in addition to van der Waals forces.
Supporting information
CCDC reference: 289652
Key indicators
- Single-crystal X-ray study
- T = 293 K
- Mean (C-C) = 0.003 Å
- R factor = 0.063
- wR factor = 0.151
- Data-to-parameter ratio = 17.9
checkCIF/PLATON results
No syntax errors found
Alert level C
PLAT199_ALERT_1_C Check the Reported _cell_measurement_temperature 293 K
PLAT200_ALERT_1_C Check the Reported _diffrn_ambient_temperature . 293 K
PLAT242_ALERT_2_C Check Low Ueq as Compared to Neighbors for N2
0 ALERT level A = In general: serious problem
0 ALERT level B = Potentially serious problem
3 ALERT level C = Check and explain
0 ALERT level G = General alerts; check
2 ALERT type 1 CIF construction/syntax error, inconsistent or missing data
1 ALERT type 2 Indicator that the structure model may be wrong or deficient
0 ALERT type 3 Indicator that the structure quality may be low
0 ALERT type 4 Improvement, methodology, query or suggestion
Data collection: SMART (Bruker, 2001); cell refinement: SAINT (Bruker, 2001); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: ORTEP-3 (Farrugia, 1997) and PLATON (Spek, 2003); software used to prepare material for publication: SHELXL97 and PARST (Nardelli, 1995).
3'-Nitro-4'-(4-methylphenyl)spiro[1
H-indole-3,2'-pyrrolidin]-2-one
top
Crystal data top
C19H19N3O3 | F(000) = 1424 |
Mr = 337.37 | Dx = 1.286 Mg m−3 |
Orthorhombic, Pbca | Mo Kα radiation, λ = 0.71073 Å |
Hall symbol: -P 2ac 2ab | Cell parameters from 9788 reflections |
a = 9.8697 (8) Å | θ = 2.7–26.6° |
b = 16.4460 (14) Å | µ = 0.09 mm−1 |
c = 21.4643 (18) Å | T = 293 K |
V = 3484.0 (5) Å3 | Needle, colourless |
Z = 8 | 0.26 × 0.24 × 0.16 mm |
Data collection top
Bruker SMART APEX CCD area-detector diffractometer | 2927 reflections with I > 2σ(I) |
Radiation source: fine-focus sealed tube | Rint = 0.040 |
Graphite monochromator | θmax = 28.0°, θmin = 1.9° |
ω scans | h = −12→12 |
19862 measured reflections | k = −21→21 |
4074 independent reflections | l = −28→28 |
Refinement top
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)] = 0.063 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.151 | H-atom parameters constrained |
S = 1.05 | w = 1/[σ2(Fo2) + (0.0679P)2 + 1.113P] where P = (Fo2 + 2Fc2)/3 |
4074 reflections | (Δ/σ)max < 0.001 |
228 parameters | Δρmax = 0.32 e Å−3 |
0 restraints | Δρmin = −0.22 e Å−3 |
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. |
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 >
σ(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. |
Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top | x | y | z | Uiso*/Ueq | |
O1 | 0.6785 (2) | −0.03633 (12) | 0.75824 (9) | 0.0790 (6) | |
O2 | 0.53068 (18) | −0.03809 (11) | 0.68526 (9) | 0.0685 (5) | |
O3 | 0.55958 (15) | 0.08385 (8) | 0.55150 (7) | 0.0495 (4) | |
N1 | 0.83831 (17) | 0.10537 (10) | 0.60134 (7) | 0.0399 (4) | |
N2 | 0.63192 (18) | −0.01088 (10) | 0.70990 (8) | 0.0437 (4) | |
N3 | 0.63777 (18) | −0.04685 (9) | 0.54111 (7) | 0.0405 (4) | |
H3 | 0.5817 | −0.0637 | 0.5133 | 0.049* | |
C1 | 0.9061 (2) | 0.12902 (14) | 0.65932 (10) | 0.0508 (6) | |
H1A | 0.9118 | 0.1878 | 0.6624 | 0.061* | |
H1B | 0.9970 | 0.1067 | 0.6608 | 0.061* | |
C2 | 0.81962 (19) | 0.09440 (12) | 0.71272 (9) | 0.0385 (4) | |
H2 | 0.8695 | 0.0494 | 0.7319 | 0.046* | |
C3 | 0.69853 (18) | 0.05920 (11) | 0.67768 (8) | 0.0334 (4) | |
H3A | 0.6312 | 0.1024 | 0.6720 | 0.040* | |
C4 | 0.75389 (19) | 0.03472 (10) | 0.61325 (8) | 0.0324 (4) | |
C5 | 0.9265 (3) | 0.10052 (15) | 0.54748 (10) | 0.0589 (6) | |
H5A | 0.9955 | 0.0605 | 0.5548 | 0.088* | |
H5B | 0.9681 | 0.1525 | 0.5404 | 0.088* | |
H5C | 0.8744 | 0.0854 | 0.5115 | 0.088* | |
C6 | 0.77974 (19) | 0.15362 (11) | 0.76347 (8) | 0.0369 (4) | |
C7 | 0.7164 (2) | 0.22615 (13) | 0.74940 (10) | 0.0510 (6) | |
H7 | 0.7009 | 0.2397 | 0.7079 | 0.061* | |
C8 | 0.6756 (2) | 0.27894 (13) | 0.79562 (10) | 0.0524 (6) | |
H8 | 0.6321 | 0.3271 | 0.7848 | 0.063* | |
C9 | 0.6983 (2) | 0.26156 (12) | 0.85756 (9) | 0.0440 (5) | |
C10 | 0.7627 (2) | 0.18956 (13) | 0.87130 (9) | 0.0460 (5) | |
H10 | 0.7795 | 0.1766 | 0.9128 | 0.055* | |
C11 | 0.8029 (2) | 0.13614 (12) | 0.82544 (9) | 0.0406 (5) | |
H11 | 0.8460 | 0.0879 | 0.8363 | 0.049* | |
C12 | 0.6536 (3) | 0.32038 (16) | 0.90779 (12) | 0.0716 (8) | |
H12A | 0.5573 | 0.3162 | 0.9135 | 0.107* | |
H12B | 0.6763 | 0.3748 | 0.8956 | 0.107* | |
H12C | 0.6987 | 0.3074 | 0.9461 | 0.107* | |
C13 | 0.6373 (2) | 0.02887 (11) | 0.56493 (8) | 0.0361 (4) | |
C14 | 0.7410 (2) | −0.09521 (11) | 0.56721 (8) | 0.0359 (4) | |
C15 | 0.7700 (2) | −0.17548 (12) | 0.55498 (9) | 0.0459 (5) | |
H15 | 0.7177 | −0.2057 | 0.5273 | 0.055* | |
C16 | 0.8798 (2) | −0.20961 (13) | 0.58526 (10) | 0.0516 (6) | |
H16 | 0.9022 | −0.2636 | 0.5776 | 0.062* | |
C17 | 0.9563 (2) | −0.16496 (14) | 0.62651 (11) | 0.0531 (6) | |
H17 | 1.0305 | −0.1889 | 0.6459 | 0.064* | |
C18 | 0.9240 (2) | −0.08459 (13) | 0.63944 (10) | 0.0437 (5) | |
H18 | 0.9750 | −0.0548 | 0.6678 | 0.052* | |
C19 | 0.81505 (19) | −0.04959 (11) | 0.60957 (8) | 0.0340 (4) | |
Atomic displacement parameters (Å2) top | U11 | U22 | U33 | U12 | U13 | U23 |
O1 | 0.0848 (14) | 0.0883 (13) | 0.0641 (11) | −0.0188 (11) | −0.0038 (10) | 0.0293 (10) |
O2 | 0.0512 (10) | 0.0700 (11) | 0.0845 (12) | −0.0280 (9) | 0.0017 (9) | −0.0016 (9) |
O3 | 0.0546 (9) | 0.0380 (8) | 0.0559 (9) | 0.0082 (7) | −0.0246 (7) | −0.0072 (6) |
N1 | 0.0410 (10) | 0.0410 (9) | 0.0377 (9) | −0.0097 (7) | 0.0013 (7) | −0.0043 (7) |
N2 | 0.0387 (10) | 0.0455 (10) | 0.0468 (10) | −0.0040 (8) | 0.0105 (8) | −0.0045 (8) |
N3 | 0.0462 (10) | 0.0357 (8) | 0.0397 (9) | 0.0012 (7) | −0.0134 (7) | −0.0076 (7) |
C1 | 0.0396 (12) | 0.0665 (14) | 0.0463 (12) | −0.0178 (10) | 0.0036 (9) | −0.0170 (10) |
C2 | 0.0319 (10) | 0.0470 (11) | 0.0366 (10) | −0.0014 (8) | −0.0042 (8) | −0.0063 (8) |
C3 | 0.0294 (10) | 0.0342 (9) | 0.0365 (10) | −0.0016 (8) | −0.0003 (7) | −0.0049 (7) |
C4 | 0.0298 (9) | 0.0338 (9) | 0.0336 (9) | −0.0003 (8) | −0.0032 (7) | −0.0027 (7) |
C5 | 0.0673 (16) | 0.0649 (15) | 0.0446 (12) | −0.0155 (13) | 0.0126 (11) | −0.0011 (11) |
C6 | 0.0336 (10) | 0.0426 (10) | 0.0345 (10) | −0.0054 (8) | −0.0037 (8) | −0.0061 (8) |
C7 | 0.0692 (16) | 0.0490 (12) | 0.0349 (10) | 0.0048 (11) | −0.0111 (10) | −0.0008 (9) |
C8 | 0.0644 (15) | 0.0391 (11) | 0.0536 (13) | 0.0055 (10) | −0.0089 (11) | −0.0028 (9) |
C9 | 0.0403 (11) | 0.0464 (12) | 0.0454 (12) | −0.0057 (9) | −0.0012 (9) | −0.0118 (9) |
C10 | 0.0467 (12) | 0.0584 (13) | 0.0327 (10) | −0.0006 (10) | −0.0047 (9) | −0.0055 (9) |
C11 | 0.0373 (11) | 0.0452 (11) | 0.0395 (11) | 0.0028 (9) | −0.0077 (8) | −0.0014 (8) |
C12 | 0.0831 (19) | 0.0700 (17) | 0.0618 (15) | 0.0111 (15) | 0.0002 (14) | −0.0246 (13) |
C13 | 0.0396 (11) | 0.0335 (10) | 0.0352 (9) | −0.0009 (8) | −0.0062 (8) | −0.0031 (8) |
C14 | 0.0387 (10) | 0.0366 (10) | 0.0325 (9) | 0.0016 (8) | 0.0032 (8) | 0.0009 (7) |
C15 | 0.0607 (14) | 0.0364 (11) | 0.0405 (11) | 0.0011 (10) | 0.0039 (10) | −0.0046 (8) |
C16 | 0.0694 (16) | 0.0364 (11) | 0.0491 (12) | 0.0143 (11) | 0.0167 (11) | 0.0036 (9) |
C17 | 0.0473 (13) | 0.0570 (13) | 0.0551 (13) | 0.0195 (11) | 0.0056 (11) | 0.0093 (11) |
C18 | 0.0346 (11) | 0.0526 (12) | 0.0440 (11) | 0.0069 (9) | −0.0024 (9) | −0.0007 (9) |
C19 | 0.0340 (10) | 0.0375 (9) | 0.0304 (9) | 0.0009 (8) | 0.0038 (7) | −0.0016 (7) |
Geometric parameters (Å, º) top
O1—N2 | 1.210 (2) | C6—C7 | 1.380 (3) |
O2—N2 | 1.216 (2) | C7—C8 | 1.378 (3) |
O3—C13 | 1.220 (2) | C7—H7 | 0.9300 |
N1—C5 | 1.449 (3) | C8—C9 | 1.378 (3) |
N1—C4 | 1.452 (2) | C8—H8 | 0.9300 |
N1—C1 | 1.465 (2) | C9—C10 | 1.376 (3) |
N2—C3 | 1.496 (2) | C9—C12 | 1.514 (3) |
N3—C13 | 1.346 (2) | C10—C11 | 1.378 (3) |
N3—C14 | 1.409 (2) | C10—H10 | 0.9300 |
N3—H3 | 0.8600 | C11—H11 | 0.9300 |
C1—C2 | 1.538 (3) | C12—H12A | 0.9600 |
C1—H1A | 0.9700 | C12—H12B | 0.9600 |
C1—H1B | 0.9700 | C12—H12C | 0.9600 |
C2—C6 | 1.513 (3) | C14—C15 | 1.376 (3) |
C2—C3 | 1.526 (2) | C14—C19 | 1.387 (3) |
C2—H2 | 0.9800 | C15—C16 | 1.382 (3) |
C3—C4 | 1.540 (2) | C15—H15 | 0.9300 |
C3—H3A | 0.9800 | C16—C17 | 1.376 (3) |
C4—C19 | 1.514 (2) | C16—H16 | 0.9300 |
C4—C13 | 1.552 (3) | C17—C18 | 1.388 (3) |
C5—H5A | 0.9600 | C17—H17 | 0.9300 |
C5—H5B | 0.9600 | C18—C19 | 1.378 (3) |
C5—H5C | 0.9600 | C18—H18 | 0.9300 |
C6—C11 | 1.380 (3) | | |
| | | |
C5—N1—C4 | 116.2 (2) | C8—C7—C6 | 121.27 (19) |
C5—N1—C1 | 114.7 (2) | C8—C7—H7 | 119.4 |
C4—N1—C1 | 109.0 (2) | C6—C7—H7 | 119.4 |
O1—N2—O2 | 124.0 (2) | C9—C8—C7 | 121.1 (2) |
O1—N2—C3 | 119.7 (2) | C9—C8—H8 | 119.5 |
O2—N2—C3 | 116.32 (18) | C7—C8—H8 | 119.5 |
C13—N3—C14 | 111.95 (16) | C10—C9—C8 | 117.41 (19) |
C13—N3—H3 | 124.0 | C10—C9—C12 | 122.1 (2) |
C14—N3—H3 | 124.0 | C8—C9—C12 | 120.5 (2) |
N1—C1—C2 | 106.34 (15) | C9—C10—C11 | 121.91 (19) |
N1—C1—H1A | 110.5 | C9—C10—H10 | 119.0 |
C2—C1—H1A | 110.5 | C11—C10—H10 | 119.0 |
N1—C1—H1B | 110.5 | C10—C11—C6 | 120.54 (19) |
C2—C1—H1B | 110.5 | C10—C11—H11 | 119.7 |
H1A—C1—H1B | 108.7 | C6—C11—H11 | 119.7 |
C6—C2—C3 | 113.28 (15) | C9—C12—H12A | 109.5 |
C6—C2—C1 | 116.26 (17) | C9—C12—H12B | 109.5 |
C3—C2—C1 | 101.98 (15) | H12A—C12—H12B | 109.5 |
C6—C2—H2 | 108.3 | C9—C12—H12C | 109.5 |
C3—C2—H2 | 108.3 | H12A—C12—H12C | 109.5 |
C1—C2—H2 | 108.3 | H12B—C12—H12C | 109.5 |
N2—C3—C2 | 114.10 (16) | O3—C13—N3 | 126.73 (17) |
N2—C3—C4 | 111.69 (14) | O3—C13—C4 | 125.30 (16) |
C2—C3—C4 | 105.30 (14) | N3—C13—C4 | 107.97 (16) |
N2—C3—H3A | 108.5 | C15—C14—C19 | 122.29 (19) |
C2—C3—H3A | 108.5 | C15—C14—N3 | 128.05 (18) |
C4—C3—H3A | 108.5 | C19—C14—N3 | 109.66 (16) |
N1—C4—C19 | 119.65 (16) | C14—C15—C16 | 117.6 (2) |
N1—C4—C3 | 98.77 (13) | C14—C15—H15 | 121.2 |
C19—C4—C3 | 115.31 (14) | C16—C15—H15 | 121.2 |
N1—C4—C13 | 110.94 (14) | C17—C16—C15 | 121.07 (19) |
C19—C4—C13 | 101.76 (14) | C17—C16—H16 | 119.5 |
C3—C4—C13 | 110.68 (15) | C15—C16—H16 | 119.5 |
N1—C5—H5A | 109.5 | C16—C17—C18 | 120.7 (2) |
N1—C5—H5B | 109.5 | C16—C17—H17 | 119.7 |
H5A—C5—H5B | 109.5 | C18—C17—H17 | 119.7 |
N1—C5—H5C | 109.5 | C19—C18—C17 | 119.0 (2) |
H5A—C5—H5C | 109.5 | C19—C18—H18 | 120.5 |
H5B—C5—H5C | 109.5 | C17—C18—H18 | 120.5 |
C11—C6—C7 | 117.78 (18) | C18—C19—C14 | 119.36 (18) |
C11—C6—C2 | 121.10 (18) | C18—C19—C4 | 132.01 (17) |
C7—C6—C2 | 121.11 (17) | C14—C19—C4 | 108.63 (16) |
| | | |
C5—N1—C1—C2 | −154.9 (2) | C8—C9—C10—C11 | −0.3 (3) |
C4—N1—C1—C2 | −22.8 (2) | C12—C9—C10—C11 | 179.9 (2) |
N1—C1—C2—C6 | −128.77 (18) | C9—C10—C11—C6 | 0.2 (3) |
N1—C1—C2—C3 | −5.0 (2) | C7—C6—C11—C10 | 0.5 (3) |
O1—N2—C3—C2 | −2.7 (3) | C2—C6—C11—C10 | −178.17 (18) |
O2—N2—C3—C2 | 176.27 (17) | C14—N3—C13—O3 | −179.71 (19) |
O1—N2—C3—C4 | 116.6 (2) | C14—N3—C13—C4 | 0.2 (2) |
O2—N2—C3—C4 | −64.5 (2) | N1—C4—C13—O3 | −50.9 (3) |
C6—C2—C3—N2 | −82.3 (2) | C19—C4—C13—O3 | −179.30 (19) |
C1—C2—C3—N2 | 152.01 (17) | C3—C4—C13—O3 | 57.7 (2) |
C6—C2—C3—C4 | 154.89 (16) | N1—C4—C13—N3 | 129.15 (17) |
C1—C2—C3—C4 | 29.19 (19) | C19—C4—C13—N3 | 0.8 (2) |
C5—N1—C4—C19 | 45.2 (2) | C3—C4—C13—N3 | −122.26 (17) |
C1—N1—C4—C19 | −86.1 (2) | C13—N3—C14—C15 | 178.7 (2) |
C5—N1—C4—C3 | 171.1 (2) | C13—N3—C14—C19 | −1.2 (2) |
C1—N1—C4—C3 | 39.69 (19) | C19—C14—C15—C16 | −1.9 (3) |
C5—N1—C4—C13 | −72.7 (2) | N3—C14—C15—C16 | 178.13 (19) |
C1—N1—C4—C13 | 155.90 (16) | C14—C15—C16—C17 | 0.5 (3) |
N2—C3—C4—N1 | −166.57 (15) | C15—C16—C17—C18 | 0.9 (3) |
C2—C3—C4—N1 | −42.21 (17) | C16—C17—C18—C19 | −1.0 (3) |
N2—C3—C4—C19 | −37.8 (2) | C17—C18—C19—C14 | −0.3 (3) |
C2—C3—C4—C19 | 86.59 (19) | C17—C18—C19—C4 | 179.75 (19) |
N2—C3—C4—C13 | 77.03 (18) | C15—C14—C19—C18 | 1.8 (3) |
C2—C3—C4—C13 | −158.61 (15) | N3—C14—C19—C18 | −178.20 (17) |
C3—C2—C6—C11 | 114.1 (2) | C15—C14—C19—C4 | −178.23 (18) |
C1—C2—C6—C11 | −128.2 (2) | N3—C14—C19—C4 | 1.7 (2) |
C3—C2—C6—C7 | −64.5 (3) | N1—C4—C19—C18 | 55.8 (3) |
C1—C2—C6—C7 | 53.2 (3) | C3—C4—C19—C18 | −61.8 (3) |
C11—C6—C7—C8 | −1.0 (3) | C13—C4—C19—C18 | 178.4 (2) |
C2—C6—C7—C8 | 177.7 (2) | N1—C4—C19—C14 | −124.09 (17) |
C6—C7—C8—C9 | 0.8 (4) | C3—C4—C19—C14 | 118.32 (17) |
C7—C8—C9—C10 | −0.2 (3) | C13—C4—C19—C14 | −1.51 (19) |
C7—C8—C9—C12 | 179.7 (2) | | |
Hydrogen-bond geometry (Å, º) top
D—H···A | D—H | H···A | D···A | D—H···A |
N3—H3···O3i | 0.86 | 2.00 | 2.849 (2) | 171 |
C16—H16···O3ii | 0.93 | 2.60 | 3.525 (3) | 174 |
C18—H18···O1iii | 0.93 | 2.58 | 3.430 (3) | 153 |
Symmetry codes: (i) −x+1, −y, −z+1; (ii) −x+3/2, y−1/2, z; (iii) x+1/2, y, −z+3/2. |
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