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The title compound, C28H21ClN2O3, crystallizes in the centrosymmetric space group P21/n with one mol­ecule in the asymmetric unit. The pyrrolidine rings of pyrrolizidine adopt envelope conformations. The structure is stabilized by intramolecular C—H...O and C—H...Cl interactions. The packing is stabilized by C—H...O and N—H...O intermolecular interactions.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536803027284/na6271sup1.cif
Contains datablocks I, global

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S1600536803027284/na6271Isup2.hkl
Contains datablock I

CCDC reference: 232146

Key indicators

  • Single-crystal X-ray study
  • T = 293 K
  • Mean [sigma](C-C) = 0.003 Å
  • R factor = 0.058
  • wR factor = 0.178
  • Data-to-parameter ratio = 17.5

checkCIF/PLATON results

No syntax errors found



Alert level A PLAT029_ALERT_3_A _diffrn_measured_fraction_theta_full Low ....... 0.00 PLAT038_ALERT_1_A _diffrn_measured_fraction_theta_max Not Given . ? PLAT039_ALERT_1_A _diffrn_measured_fraction_theta_full Not Given . ?
Alert level C PLAT125_ALERT_4_C No _symmetry_space_group_name_Hall Given ....... ? PLAT220_ALERT_2_C Large Non-Solvent C Ueq(max)/Ueq(min) ... 2.73 Ratio PLAT230_ALERT_2_C Hirshfeld Test Diff for C27 - C28 = 5.52 su PLAT241_ALERT_2_C Check High U(eq) as Compared to Neighbors .... C12 PLAT716_ALERT_1_C H...A Unknown or Inconsistent Label .......... C1G H20 C1G PLAT717_ALERT_1_C D...A Unknown or Inconsistent Label .......... C1G C20 C1G PLAT718_ALERT_1_C D-H..A Unknown or Inconsistent Label .......... C1G C20 H20 C1G
3 ALERT level A = In general: serious problem 0 ALERT level B = Potentially serious problem 7 ALERT level C = Check and explain 0 ALERT level G = General alerts; check 5 ALERT type 1 CIF construction/syntax error, inconsistent or missing data 3 ALERT type 2 Indicator that the structure model may be wrong or deficient 1 ALERT type 3 Indicator that the structure quality may be low 1 ALERT type 4 Improvement, methodology, query or suggestion

Computing details top

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: ZORTEP (Zsolnai, 1997) and PLATON (Spek, 1990); software used to prepare material for publication: SHELXL97 and PARST (Nardelli, 1995).

1-(2-Cholorophenyl)-1H-indan-2-spiro-2'-pyrrolizidine-3'-spiro-3''- 1H-indole-1,3,2''(2H,3''H)-trione top
Crystal data top
C28H21ClN2O3F(000) = 976
Mr = 468.92Dx = 1.335 Mg m3
Monoclinic, P21/nMo Kα radiation, λ = 0.71073 Å
a = 10.8456 (6) ÅCell parameters from 4187 reflections
b = 14.1502 (8) Åθ = 2.3–24.3°
c = 15.2068 (9) ŵ = 0.20 mm1
β = 92.053 (1)°T = 293 K
V = 2332.3 (2) Å3Needle, pale yellow
Z = 40.18 × 0.17 × 0.11 mm
Data collection top
CCD Area-Detector
diffractometer
3882 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tubeRint = 0.023
Graphite monochromatorθmax = 28.0°, θmin = 2.0°
ω scansh = 814
14407 measured reflectionsk = 1818
5387 independent reflectionsl = 2019
Refinement top
Refinement on F2Primary atom site location: structure-invariant direct methods
Least-squares matrix: fullSecondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.058Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.178H-atom parameters constrained
S = 1.03 w = 1/[σ2(Fo2) + (0.1051P)2 + 0.4748P]
where P = (Fo2 + 2Fc2)/3
5387 reflections(Δ/σ)max < 0.001
307 parametersΔρmax = 0.48 e Å3
0 restraintsΔρmin = 0.44 e Å3
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
xyzUiso*/Ueq
Cl10.89248 (9)0.26176 (7)0.23346 (4)0.0873 (3)
N10.96749 (15)0.04470 (11)0.09583 (11)0.0405 (4)
H11.01530.00230.08360.049*
C20.87356 (18)0.04233 (14)0.16038 (12)0.0386 (4)
C30.8439 (2)0.03019 (16)0.21754 (16)0.0542 (6)
H30.88570.08750.21430.065*
C40.7506 (3)0.0155 (2)0.27946 (17)0.0663 (7)
H40.72800.06380.31820.080*
C50.6902 (3)0.0703 (2)0.28482 (17)0.0700 (8)
H50.62810.07910.32780.084*
C60.7203 (2)0.14431 (18)0.22687 (14)0.0538 (6)
H60.67980.20210.23120.065*
C70.81188 (18)0.12893 (14)0.16327 (12)0.0366 (4)
C80.86601 (16)0.19233 (12)0.09169 (11)0.0304 (4)
C90.97533 (17)0.12900 (13)0.05445 (12)0.0345 (4)
N100.90408 (15)0.28545 (11)0.12009 (10)0.0362 (4)
C111.0168 (2)0.29181 (16)0.17087 (15)0.0516 (6)
H11A0.99660.30550.23220.062*
H11B1.06280.23310.16730.062*
C121.0904 (3)0.3715 (2)0.1292 (2)0.0729 (8)
H12A1.07160.43090.15850.087*
H12B1.17820.35940.13210.087*
C131.0516 (2)0.37424 (16)0.03428 (16)0.0518 (6)
H13A1.06410.43650.00870.062*
H13B1.09640.32790.00140.062*
C140.91467 (18)0.34979 (13)0.04376 (13)0.0367 (4)
H140.86780.40760.05710.044*
C150.85482 (17)0.29784 (13)0.03223 (12)0.0354 (4)
H150.92130.26730.06710.042*
C160.77902 (16)0.21750 (12)0.01571 (11)0.0305 (4)
C170.74705 (17)0.13477 (13)0.04472 (12)0.0349 (4)
C180.61276 (18)0.12913 (14)0.05038 (13)0.0406 (4)
C190.5439 (2)0.06670 (18)0.09995 (16)0.0576 (6)
H190.58190.02290.13760.069*
C200.4175 (2)0.0725 (2)0.0908 (2)0.0741 (8)
H200.36900.03140.12240.089*
C210.3613 (2)0.1383 (2)0.0355 (2)0.0765 (9)
H210.27560.14050.03100.092*
C220.4289 (2)0.2007 (2)0.01337 (18)0.0632 (7)
H220.39040.24500.05030.076*
C230.55672 (18)0.19480 (15)0.00517 (13)0.0411 (5)
C240.65008 (17)0.25068 (13)0.05014 (13)0.0359 (4)
C250.78313 (19)0.35896 (15)0.09480 (14)0.0441 (5)
C260.7022 (2)0.42896 (17)0.06477 (18)0.0558 (6)
H260.69120.43870.00450.067*
C270.6371 (3)0.4848 (2)0.1225 (2)0.0756 (9)
H270.58230.53030.10070.091*
C280.6542 (3)0.4725 (2)0.2115 (2)0.0828 (10)
H280.61180.51060.25000.099*
C290.7327 (3)0.4048 (2)0.24404 (19)0.0780 (9)
H290.74390.39690.30450.094*
C300.7963 (2)0.34763 (19)0.18645 (15)0.0593 (7)
O311.05445 (13)0.15182 (10)0.00005 (10)0.0466 (4)
O320.62882 (14)0.31223 (11)0.10334 (10)0.0503 (4)
O330.81984 (14)0.08227 (11)0.08147 (10)0.0511 (4)
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
Cl10.1071 (7)0.1089 (7)0.0450 (4)0.0044 (5)0.0082 (4)0.0067 (4)
N10.0375 (9)0.0356 (9)0.0485 (9)0.0067 (7)0.0032 (7)0.0018 (7)
C20.0376 (10)0.0400 (10)0.0387 (10)0.0036 (8)0.0094 (8)0.0028 (8)
C30.0545 (14)0.0462 (12)0.0624 (14)0.0037 (10)0.0117 (11)0.0185 (11)
C40.0678 (16)0.0753 (18)0.0555 (14)0.0068 (14)0.0007 (12)0.0318 (13)
C50.0696 (17)0.086 (2)0.0526 (14)0.0005 (15)0.0209 (13)0.0215 (13)
C60.0561 (14)0.0603 (14)0.0438 (12)0.0059 (11)0.0131 (10)0.0063 (10)
C70.0360 (10)0.0402 (10)0.0338 (9)0.0039 (8)0.0020 (7)0.0027 (8)
C80.0274 (8)0.0314 (9)0.0324 (8)0.0002 (7)0.0006 (7)0.0012 (7)
C90.0302 (9)0.0371 (10)0.0365 (9)0.0011 (7)0.0033 (7)0.0051 (7)
N100.0406 (9)0.0311 (8)0.0371 (8)0.0026 (6)0.0037 (7)0.0026 (6)
C110.0564 (14)0.0466 (12)0.0531 (13)0.0053 (10)0.0197 (11)0.0021 (10)
C120.0605 (16)0.0716 (17)0.0882 (19)0.0242 (13)0.0264 (14)0.0051 (15)
C130.0442 (12)0.0422 (12)0.0693 (15)0.0129 (9)0.0046 (11)0.0068 (10)
C140.0363 (10)0.0308 (9)0.0431 (10)0.0020 (7)0.0011 (8)0.0011 (8)
C150.0317 (9)0.0370 (10)0.0373 (9)0.0027 (7)0.0013 (7)0.0034 (8)
C160.0274 (8)0.0308 (9)0.0332 (9)0.0007 (7)0.0009 (7)0.0008 (7)
C170.0345 (9)0.0355 (9)0.0350 (9)0.0010 (7)0.0041 (7)0.0003 (7)
C180.0345 (10)0.0439 (11)0.0438 (10)0.0040 (8)0.0063 (8)0.0011 (9)
C190.0500 (13)0.0625 (15)0.0612 (14)0.0087 (11)0.0161 (11)0.0086 (12)
C200.0469 (14)0.095 (2)0.0822 (19)0.0210 (14)0.0205 (13)0.0086 (16)
C210.0297 (11)0.113 (2)0.087 (2)0.0090 (13)0.0101 (12)0.0028 (18)
C220.0329 (11)0.0865 (18)0.0700 (16)0.0035 (12)0.0014 (11)0.0037 (14)
C230.0298 (9)0.0490 (11)0.0446 (11)0.0000 (8)0.0011 (8)0.0024 (9)
C240.0328 (9)0.0364 (10)0.0382 (10)0.0038 (7)0.0022 (8)0.0034 (8)
C250.0389 (11)0.0481 (12)0.0458 (11)0.0104 (9)0.0068 (9)0.0132 (9)
C260.0466 (12)0.0503 (13)0.0707 (15)0.0007 (10)0.0071 (11)0.0168 (11)
C270.0542 (15)0.0594 (16)0.115 (3)0.0036 (12)0.0239 (16)0.0284 (16)
C280.076 (2)0.086 (2)0.090 (2)0.0213 (17)0.0472 (18)0.0383 (18)
C290.087 (2)0.091 (2)0.0576 (15)0.0349 (18)0.0327 (15)0.0275 (15)
C300.0609 (15)0.0685 (16)0.0493 (13)0.0240 (12)0.0123 (11)0.0150 (11)
O310.0342 (7)0.0508 (8)0.0540 (8)0.0037 (6)0.0085 (6)0.0006 (7)
O320.0450 (8)0.0479 (8)0.0574 (9)0.0091 (7)0.0057 (7)0.0130 (7)
O330.0411 (8)0.0553 (9)0.0574 (9)0.0109 (7)0.0077 (7)0.0227 (7)
Geometric parameters (Å, º) top
Cl1—C301.739 (3)C14—H140.9800
N1—C91.350 (2)C15—C251.520 (3)
N1—C21.390 (3)C15—C161.567 (2)
N1—H10.8600C15—H150.9800
C2—C31.376 (3)C16—C171.536 (3)
C2—C71.396 (3)C16—C241.548 (2)
C3—C41.373 (4)C17—O331.207 (2)
C3—H30.9300C17—C181.464 (3)
C4—C51.381 (4)C18—C231.382 (3)
C4—H40.9300C18—C191.395 (3)
C5—C61.400 (3)C19—C201.376 (4)
C5—H50.9300C19—H190.9300
C6—C71.378 (3)C20—C211.381 (4)
C6—H60.9300C20—H200.9300
C7—C81.513 (2)C21—C221.382 (4)
C8—N101.451 (2)C21—H210.9300
C8—C161.559 (2)C22—C231.390 (3)
C8—C91.575 (2)C22—H220.9300
C9—O311.215 (2)C23—C241.472 (3)
N10—C111.472 (3)C24—O321.205 (2)
N10—C141.476 (2)C25—C261.390 (3)
C11—C121.508 (3)C25—C301.405 (3)
C11—H11A0.9700C26—C271.391 (3)
C11—H11B0.9700C26—H260.9300
C12—C131.518 (4)C27—C281.371 (5)
C12—H12A0.9700C27—H270.9300
C12—H12B0.9700C28—C291.362 (5)
C13—C141.527 (3)C28—H280.9300
C13—H13A0.9700C29—C301.393 (4)
C13—H13B0.9700C29—H290.9300
C14—C151.533 (3)
C9—N1—C2112.5 (2)C15—C14—H14109.0
C9—N1—H1123.7C25—C15—C14116.03 (16)
C2—N1—H1123.7C25—C15—C16115.61 (15)
C3—C2—N1127.8 (2)C14—C15—C16103.08 (14)
C3—C2—C7122.3 (2)C25—C15—H15107.2
N1—C2—C7109.84 (16)C14—C15—H15107.2
C4—C3—C2118.1 (2)C16—C15—H15107.2
C4—C3—H3121.0C17—C16—C24102.29 (14)
C2—C3—H3121.0C17—C16—C8115.15 (14)
C3—C4—C5120.7 (2)C24—C16—C8112.45 (14)
C3—C4—H4119.7C17—C16—C15113.61 (14)
C5—C4—H4119.7C24—C16—C15112.93 (14)
C4—C5—C6121.4 (2)C8—C16—C15100.91 (13)
C4—C5—H5119.3O33—C17—C18125.09 (18)
C6—C5—H5119.3O33—C17—C16126.06 (17)
C7—C6—C5118.0 (2)C18—C17—C16108.85 (15)
C7—C6—H6121.0C23—C18—C19121.59 (19)
C5—C6—H6121.0C23—C18—C17110.12 (17)
C6—C7—C2119.5 (2)C19—C18—C17128.2 (2)
C6—C7—C8131.49 (18)C20—C19—C18117.2 (2)
C2—C7—C8108.95 (16)C20—C19—H19121.4
N10—C8—C7115.6 (2)C18—C19—H19121.4
N10—C8—C16101.50 (14)C19—C20—C21121.3 (2)
C7—C8—C16116.06 (14)C19—C20—H20119.4
N10—C8—C9113.89 (14)C21—C20—H20119.4
C7—C8—C9100.89 (14)C20—C21—C22121.8 (2)
C16—C8—C9109.34 (13)C20—C21—H21119.1
O31—C9—N1125.72 (18)C22—C21—H21119.1
O31—C9—C8126.73 (17)C21—C22—C23117.4 (2)
N1—C9—C8107.52 (15)C21—C22—H22121.3
C8—N10—C11117.5 (2)C23—C22—H22121.3
C8—N10—C14109.9 (1)C18—C23—C22120.7 (2)
C11—N10—C14109.4 (2)C18—C23—C24110.50 (17)
N10—C11—C12105.21 (18)C22—C23—C24128.8 (2)
N10—C11—H11A110.7O32—C24—C23125.56 (18)
C12—C11—H11A110.7O32—C24—C16126.49 (17)
N10—C11—H11B110.7C23—C24—C16107.94 (15)
C12—C11—H11B110.7C26—C25—C30116.6 (2)
H11A—C11—H11B108.8C26—C25—C15122.07 (19)
C11—C12—C13104.98 (19)C30—C25—C15121.3 (2)
C11—C12—H12A110.8C25—C26—C27121.7 (3)
C13—C12—H12A110.8C25—C26—H26119.1
C11—C12—H12B110.8C27—C26—H26119.1
C13—C12—H12B110.8C28—C27—C26119.8 (3)
H12A—C12—H12B108.8C28—C27—H27120.1
C12—C13—C14101.90 (19)C26—C27—H27120.1
C12—C13—H13A111.4C29—C28—C27120.6 (3)
C14—C13—H13A111.4C29—C28—H28119.7
C12—C13—H13B111.4C27—C28—H28119.7
C14—C13—H13B111.4C28—C29—C30119.8 (3)
H13A—C13—H13B109.3C28—C29—H29120.1
N10—C14—C13105.19 (16)C30—C29—H29120.1
N10—C14—C15105.89 (14)C29—C30—C25121.5 (3)
C13—C14—C15118.31 (17)C29—C30—Cl1116.8 (2)
N10—C14—H14109.0C25—C30—Cl1121.71 (19)
C13—C14—H14109.0
C9—N1—C2—C3176.6 (2)C7—C8—C16—C15168.77 (15)
C9—N1—C2—C70.8 (2)C9—C8—C16—C1577.99 (16)
N1—C2—C3—C4176.8 (2)C25—C15—C16—C1772.7 (2)
C7—C2—C3—C40.4 (3)C14—C15—C16—C17159.62 (15)
C2—C3—C4—C51.1 (4)C25—C15—C16—C2443.2 (2)
C3—C4—C5—C61.0 (4)C14—C15—C16—C2484.45 (17)
C4—C5—C6—C70.6 (4)C25—C15—C16—C8163.47 (16)
C5—C6—C7—C22.0 (3)C14—C15—C16—C835.80 (16)
C5—C6—C7—C8180.0 (2)C24—C16—C17—O33174.26 (19)
C3—C2—C7—C62.0 (3)C8—C16—C17—O3352.0 (3)
N1—C2—C7—C6175.64 (18)C15—C16—C17—O3363.7 (2)
C3—C2—C7—C8179.61 (18)C24—C16—C17—C185.38 (19)
N1—C2—C7—C82.8 (2)C8—C16—C17—C18127.67 (16)
C6—C7—C8—N1050.2 (3)C15—C16—C17—C18116.66 (17)
C2—C7—C8—N10127.98 (17)O33—C17—C18—C23175.1 (2)
C6—C7—C8—C1668.5 (3)C16—C17—C18—C234.5 (2)
C2—C7—C8—C16113.34 (17)O33—C17—C18—C192.5 (4)
C6—C7—C8—C9173.5 (2)C16—C17—C18—C19177.8 (2)
C2—C7—C8—C94.67 (18)C23—C18—C19—C200.5 (4)
C2—N1—C9—O31174.56 (18)C17—C18—C19—C20176.9 (2)
C2—N1—C9—C83.9 (2)C18—C19—C20—C210.7 (4)
N10—C8—C9—O3148.9 (2)C19—C20—C21—C220.3 (5)
C7—C8—C9—O31173.33 (18)C20—C21—C22—C230.3 (4)
C16—C8—C9—O3163.9 (2)C19—C18—C23—C220.0 (3)
N10—C8—C9—N1129.59 (16)C17—C18—C23—C22177.9 (2)
C7—C8—C9—N15.12 (18)C19—C18—C23—C24179.3 (2)
C16—C8—C9—N1117.68 (16)C17—C18—C23—C241.5 (2)
C7—C8—N10—C1173.1 (2)C21—C22—C23—C180.5 (4)
C16—C8—N10—C11160.44 (16)C21—C22—C23—C24178.8 (2)
C9—C8—N10—C1143.1 (2)C18—C23—C24—O32178.9 (2)
C7—C8—N10—C14160.93 (15)C22—C23—C24—O320.4 (4)
C16—C8—N10—C1434.48 (17)C18—C23—C24—C162.1 (2)
C9—C8—N10—C1482.90 (18)C22—C23—C24—C16178.6 (2)
C8—N10—C11—C12133.1 (2)C17—C16—C24—O32176.51 (19)
C14—N10—C11—C126.8 (2)C8—C16—C24—O3252.4 (2)
N10—C11—C12—C1327.3 (3)C15—C16—C24—O3261.0 (2)
C11—C12—C13—C1436.4 (3)C17—C16—C24—C234.49 (18)
C8—N10—C14—C13114.38 (17)C8—C16—C24—C23128.59 (16)
C11—N10—C14—C1316.1 (2)C15—C16—C24—C23118.01 (17)
C8—N10—C14—C1511.64 (19)C14—C15—C25—C2644.5 (3)
C11—N10—C14—C15142.09 (16)C16—C15—C25—C2676.4 (2)
C12—C13—C14—N1032.0 (2)C14—C15—C25—C30135.1 (2)
C12—C13—C14—C15149.9 (2)C16—C15—C25—C30104.0 (2)
N10—C14—C15—C25143.60 (16)C30—C25—C26—C270.2 (3)
C13—C14—C15—C2598.8 (2)C15—C25—C26—C27179.8 (2)
N10—C14—C15—C1616.20 (18)C25—C26—C27—C281.3 (4)
C13—C14—C15—C16133.76 (17)C26—C27—C28—C291.2 (4)
N10—C8—C16—C17165.38 (14)C27—C28—C29—C300.0 (4)
C7—C8—C16—C1768.48 (19)C28—C29—C30—C251.1 (4)
C9—C8—C16—C1744.76 (19)C28—C29—C30—Cl1178.9 (2)
N10—C8—C16—C2477.97 (16)C26—C25—C30—C291.0 (3)
C7—C8—C16—C2448.2 (2)C15—C25—C30—C29178.6 (2)
C9—C8—C16—C24161.41 (14)C26—C25—C30—Cl1179.03 (17)
N10—C8—C16—C1542.63 (15)C15—C25—C30—Cl11.3 (3)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
C6—H6···O320.932.573.208 (3)127
C13—H13B···O310.972.533.190 (3)125
C15—H15···Cl10.982.563.115 (2)116
C15—H15···O310.982.433.045 (2)121
C26—H26···O320.932.503.123 (3)124
N1—H1···O31i0.862.593.152 (2)124
N1—H1···O33i0.862.112.926 (2)157
C21—H21···O31ii0.932.433.357 (3)173
C20—H20···C1giii0.932.593.508 (4)170
Symmetry codes: (i) x+2, y, z; (ii) x1, y, z; (iii) x+1, y, z.
 

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