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In the title compound, C28H24N2O4S, the indole ring system is planar, but the pyrrolidine and thia­zole rings adopt an envelope and a twist conformation, respectively. The indole system makes a dihedral angle of 55.7 (1)° with the methoxy­phen­yl ring. The mol­ecular packing in the crystal structure is stabilized by C—H...O and N—H...O hydrogen bonds.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536805013218/bt6657sup1.cif
Contains datablocks I, global

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S1600536805013218/bt6657Isup2.hkl
Contains datablock I

CCDC reference: 274339

Key indicators

  • Single-crystal X-ray study
  • T = 273 K
  • Mean [sigma](C-C) = 0.002 Å
  • R factor = 0.047
  • wR factor = 0.126
  • Data-to-parameter ratio = 16.2

checkCIF/PLATON results

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Alert level C PLAT029_ALERT_3_C _diffrn_measured_fraction_theta_full Low ....... 0.96
0 ALERT level A = In general: serious problem 0 ALERT level B = Potentially serious problem 1 ALERT level C = Check and explain 0 ALERT level G = General alerts; check 0 ALERT type 1 CIF construction/syntax error, inconsistent or missing data 0 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 0 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: ORTEP-3 (Farrugia, 1997) and PLATON (Spek, 2003).

7'-(4-Methoxyphenyl)-chroman-3-spiro-6'-hexahydro-1H-pyrrolo[1,2-c]thiazole- 5'-spiro-3''-1''H-indole-4,2''(3''H)-dione top
Crystal data top
C28H24N2O4SF(000) = 1016
Mr = 484.55Dx = 1.371 Mg m3
Monoclinic, P21/cMo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybcCell parameters from 6089 reflections
a = 9.5561 (6) Åθ = 2.5–27.8°
b = 16.1035 (11) ŵ = 0.18 mm1
c = 15.2631 (10) ÅT = 273 K
β = 91.213 (10)°Block, colourless
V = 2348.3 (3) Å30.26 × 0.24 × 0.18 mm
Z = 4
Data collection top
Bruker SMART APEX CCD area-detector
diffractometer
4396 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tubeRint = 0.018
Graphite monochromatorθmax = 28.0°, θmin = 1.8°
ω scansh = 1011
14171 measured reflectionsk = 2021
5134 independent reflectionsl = 1920
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)] = 0.047Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.126H-atom parameters constrained
S = 1.02 w = 1/[σ2(Fo2) + (0.0726P)2 + 0.5516P]
where P = (Fo2 + 2Fc2)/3
5134 reflections(Δ/σ)max < 0.001
317 parametersΔρmax = 0.38 e Å3
0 restraintsΔρmin = 0.21 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
S10.56744 (5)0.12022 (3)0.08305 (3)0.04361 (14)
O20.04618 (13)0.12139 (7)0.20431 (8)0.0465 (3)
N10.36785 (13)0.16341 (7)0.01790 (8)0.0328 (3)
C30.43513 (16)0.16285 (9)0.16237 (10)0.0327 (3)
H30.47730.21810.15720.039*
C70.49524 (17)0.12477 (9)0.24588 (10)0.0344 (3)
N20.01777 (15)0.12082 (8)0.00367 (9)0.0404 (3)
H20.05080.08940.01990.048*
O40.16687 (13)0.02012 (6)0.04915 (8)0.0443 (3)
O30.31578 (13)0.31680 (7)0.20708 (8)0.0472 (3)
C210.23219 (17)0.26100 (9)0.19645 (10)0.0359 (3)
C280.14544 (17)0.23923 (9)0.01771 (9)0.0347 (3)
O10.66593 (17)0.02539 (9)0.47656 (9)0.0617 (4)
C40.46223 (16)0.11786 (9)0.07671 (9)0.0330 (3)
H40.43470.05940.08050.040*
C20.27354 (16)0.17582 (8)0.15966 (9)0.0323 (3)
C140.19497 (18)0.11365 (10)0.21626 (11)0.0391 (4)
H14A0.22320.05770.20110.047*
H14B0.21980.12290.27740.047*
C220.13544 (17)0.09311 (9)0.03630 (10)0.0357 (3)
C60.60442 (18)0.12656 (10)0.03482 (11)0.0422 (4)
H6A0.66670.08220.05370.051*
H6B0.64710.17940.05000.051*
C10.23109 (16)0.16961 (8)0.05781 (9)0.0319 (3)
C230.02018 (17)0.20747 (10)0.01584 (10)0.0368 (3)
C200.08286 (19)0.26888 (11)0.21687 (11)0.0429 (4)
C50.37914 (19)0.13225 (10)0.07051 (10)0.0410 (4)
H5A0.34070.17150.11280.049*
H5B0.33120.07950.07740.049*
C270.17686 (19)0.32234 (10)0.00765 (11)0.0414 (4)
H270.26180.34370.02810.050*
C150.00413 (19)0.19972 (12)0.21405 (10)0.0446 (4)
C110.5560 (2)0.14161 (11)0.39999 (11)0.0468 (4)
H110.55690.17460.45000.056*
C100.60880 (19)0.06227 (11)0.40329 (11)0.0437 (4)
C120.50146 (19)0.17199 (10)0.32158 (11)0.0440 (4)
H120.46770.22620.31970.053*
C240.07878 (19)0.25713 (12)0.05644 (11)0.0471 (4)
H240.16340.23560.07740.057*
C80.54972 (19)0.04487 (10)0.25091 (11)0.0427 (4)
H80.54720.01130.20130.051*
C250.0466 (2)0.34081 (12)0.06464 (12)0.0516 (5)
H250.11130.37600.09180.062*
C90.6075 (2)0.01440 (10)0.32813 (12)0.0490 (4)
H90.64590.03870.32960.059*
C260.0786 (2)0.37323 (11)0.03376 (12)0.0489 (4)
H260.09720.42950.04070.059*
C160.1485 (2)0.20856 (15)0.22122 (12)0.0576 (5)
H160.20670.16230.21770.069*
C190.0235 (2)0.34715 (13)0.23146 (13)0.0561 (5)
H190.08040.39390.23540.067*
C180.1193 (3)0.35483 (16)0.23999 (15)0.0687 (6)
H180.15860.40670.25010.082*
C130.6682 (3)0.07218 (16)0.55563 (13)0.0722 (6)
H13A0.72800.11960.54920.108*
H13B0.70310.03810.60290.108*
H13C0.57510.09040.56820.108*
C170.2036 (2)0.28584 (18)0.23349 (14)0.0694 (6)
H170.30000.29190.23750.083*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
S10.0448 (3)0.0425 (2)0.0439 (2)0.00119 (17)0.00911 (18)0.00049 (15)
O20.0368 (7)0.0507 (7)0.0520 (7)0.0111 (5)0.0037 (5)0.0013 (5)
N10.0298 (7)0.0319 (6)0.0366 (6)0.0011 (5)0.0011 (5)0.0005 (5)
C30.0319 (9)0.0270 (6)0.0390 (7)0.0014 (5)0.0017 (6)0.0019 (5)
C70.0297 (9)0.0331 (7)0.0401 (8)0.0004 (6)0.0036 (6)0.0032 (6)
N20.0321 (8)0.0401 (7)0.0486 (7)0.0070 (5)0.0069 (6)0.0049 (5)
O40.0399 (7)0.0307 (5)0.0622 (7)0.0053 (5)0.0040 (5)0.0041 (5)
O30.0471 (8)0.0308 (5)0.0634 (7)0.0018 (5)0.0034 (6)0.0067 (5)
C210.0392 (9)0.0322 (7)0.0363 (7)0.0024 (6)0.0024 (6)0.0012 (5)
C280.0330 (9)0.0346 (7)0.0363 (7)0.0012 (6)0.0018 (6)0.0017 (6)
O10.0740 (10)0.0618 (8)0.0484 (7)0.0049 (7)0.0167 (7)0.0078 (6)
C40.0318 (9)0.0293 (7)0.0379 (7)0.0003 (6)0.0015 (6)0.0004 (5)
C20.0313 (9)0.0286 (6)0.0370 (7)0.0019 (6)0.0027 (6)0.0006 (5)
C140.0356 (10)0.0384 (8)0.0434 (8)0.0054 (6)0.0003 (7)0.0044 (6)
C220.0322 (9)0.0351 (7)0.0399 (8)0.0059 (6)0.0003 (6)0.0050 (6)
C60.0360 (10)0.0453 (9)0.0455 (9)0.0023 (7)0.0016 (7)0.0024 (7)
C10.0300 (9)0.0272 (6)0.0384 (7)0.0033 (5)0.0033 (6)0.0016 (5)
C230.0331 (9)0.0418 (8)0.0355 (7)0.0004 (6)0.0002 (6)0.0024 (6)
C200.0397 (10)0.0497 (9)0.0392 (8)0.0071 (7)0.0015 (7)0.0024 (7)
C50.0433 (10)0.0419 (8)0.0378 (8)0.0055 (7)0.0005 (7)0.0006 (6)
C270.0413 (10)0.0365 (8)0.0462 (9)0.0013 (7)0.0025 (7)0.0010 (6)
C150.0376 (10)0.0613 (10)0.0349 (8)0.0002 (8)0.0022 (6)0.0014 (7)
C110.0506 (11)0.0477 (9)0.0416 (8)0.0015 (8)0.0080 (7)0.0102 (7)
C100.0393 (10)0.0472 (9)0.0443 (9)0.0025 (7)0.0072 (7)0.0040 (7)
C120.0468 (11)0.0369 (8)0.0478 (9)0.0065 (7)0.0087 (7)0.0088 (6)
C240.0363 (10)0.0600 (10)0.0448 (9)0.0038 (8)0.0056 (7)0.0013 (7)
C80.0505 (11)0.0346 (8)0.0427 (8)0.0048 (7)0.0036 (7)0.0057 (6)
C250.0473 (12)0.0560 (10)0.0511 (10)0.0157 (8)0.0047 (8)0.0093 (8)
C90.0575 (12)0.0367 (8)0.0523 (10)0.0096 (8)0.0062 (8)0.0002 (7)
C260.0542 (12)0.0394 (8)0.0532 (10)0.0074 (8)0.0015 (8)0.0071 (7)
C160.0383 (12)0.0889 (15)0.0458 (10)0.0037 (10)0.0035 (8)0.0016 (9)
C190.0563 (13)0.0562 (11)0.0559 (11)0.0159 (9)0.0055 (9)0.0032 (8)
C180.0600 (15)0.0817 (15)0.0647 (13)0.0331 (12)0.0087 (10)0.0026 (11)
C130.0853 (17)0.0861 (16)0.0445 (10)0.0101 (13)0.0136 (10)0.0052 (10)
C170.0408 (13)0.1097 (19)0.0577 (12)0.0178 (12)0.0056 (9)0.0006 (12)
Geometric parameters (Å, º) top
S1—C51.824 (2)C6—H6B0.9700
S1—C61.829 (2)C23—C241.376 (2)
O2—C151.359 (2)C20—C151.390 (3)
O2—C141.435 (2)C20—C191.402 (2)
N1—C51.446 (2)C5—H5A0.9700
N1—C11.457 (2)C5—H5B0.9700
N1—C41.4570 (19)C27—C261.389 (2)
C3—C71.516 (2)C27—H270.9300
C3—C41.522 (2)C15—C161.393 (3)
C3—C21.558 (2)C11—C101.374 (2)
C3—H30.9800C11—C121.385 (2)
C7—C121.383 (2)C11—H110.9300
C7—C81.390 (2)C10—C91.382 (2)
N2—C221.344 (2)C12—H120.9300
N2—C231.408 (2)C24—C251.389 (3)
N2—H20.8600C24—H240.9300
O4—C221.2279 (19)C8—C91.381 (2)
O3—C211.2110 (19)C8—H80.9300
C21—C201.473 (2)C25—C261.379 (3)
C21—C21.537 (2)C25—H250.9300
C28—C271.381 (2)C9—H90.9300
C28—C231.390 (2)C26—H260.9300
C28—C11.510 (2)C16—C171.366 (3)
O1—C101.370 (2)C16—H160.9300
O1—C131.423 (3)C19—C181.379 (3)
C4—C61.520 (2)C19—H190.9300
C4—H40.9800C18—C171.374 (4)
C2—C141.530 (2)C18—H180.9300
C2—C11.601 (2)C13—H13A0.9600
C14—H14A0.9700C13—H13B0.9600
C14—H14B0.9700C13—H13C0.9600
C22—C11.565 (2)C17—H170.9300
C6—H6A0.9700
C5—S1—C693.52 (8)C28—C23—N2109.43 (13)
C15—O2—C14114.74 (13)C15—C20—C19118.80 (18)
C5—N1—C1120.0 (1)C15—C20—C21120.39 (15)
C5—N1—C4110.1 (1)C19—C20—C21120.55 (17)
C1—N1—C4109.0 (1)N1—C5—S1103.18 (11)
C7—C3—C4117.47 (12)N1—C5—H5A111.1
C7—C3—C2115.74 (12)S1—C5—H5A111.1
C4—C3—C2103.16 (12)N1—C5—H5B111.1
C7—C3—H3106.6S1—C5—H5B111.1
C4—C3—H3106.6H5A—C5—H5B109.1
C2—C3—H3106.6C28—C27—C26118.42 (16)
C12—C7—C8116.97 (14)C28—C27—H27120.8
C12—C7—C3119.24 (13)C26—C27—H27120.8
C8—C7—C3123.76 (13)O2—C15—C20122.30 (16)
C22—N2—C23111.91 (13)O2—C15—C16117.16 (17)
C22—N2—H2124.0C20—C15—C16120.54 (18)
C23—N2—H2124.0C10—C11—C12119.43 (15)
O3—C21—C20123.17 (14)C10—C11—H11120.3
O3—C21—C2122.49 (14)C12—C11—H11120.3
C20—C21—C2114.34 (13)O1—C10—C11124.9 (2)
C27—C28—C23120.23 (15)O1—C10—C9115.6 (2)
C27—C28—C1130.34 (14)C11—C10—C9119.44 (15)
C23—C28—C1109.35 (13)C7—C12—C11122.44 (15)
C10—O1—C13117.50 (16)C7—C12—H12118.8
N1—C4—C6103.98 (12)C11—C12—H12118.8
N1—C4—C3100.09 (11)C23—C24—C25116.94 (17)
C6—C4—C3119.17 (13)C23—C24—H24121.5
N1—C4—H4110.9C25—C24—H24121.5
C6—C4—H4110.9C9—C8—C7121.24 (15)
C3—C4—H4110.9C9—C8—H8119.4
C14—C2—C21104.16 (12)C7—C8—H8119.4
C14—C2—C3113.28 (12)C26—C25—C24121.94 (16)
C21—C2—C3111.86 (12)C26—C25—H25119.0
C14—C2—C1112.96 (12)C24—C25—H25119.0
C21—C2—C1110.41 (11)C8—C9—C10120.44 (16)
C3—C2—C1104.36 (11)C8—C9—H9119.8
O2—C14—C2111.60 (13)C10—C9—H9119.8
O2—C14—H14A109.3C25—C26—C27120.38 (16)
C2—C14—H14A109.3C25—C26—H26119.8
O2—C14—H14B109.3C27—C26—H26119.8
C2—C14—H14B109.3C17—C16—C15119.3 (2)
H14A—C14—H14B108.0C17—C16—H16120.4
O4—C22—N2126.15 (14)C15—C16—H16120.4
O4—C22—C1125.47 (14)C18—C19—C20120.0 (2)
N2—C22—C1108.25 (12)C18—C19—H19120.0
C4—C6—S1104.64 (11)C20—C19—H19120.0
C4—C6—H6A110.8C17—C18—C19120.0 (2)
S1—C6—H6A110.8C17—C18—H18120.0
C4—C6—H6B110.8C19—C18—H18120.0
S1—C6—H6B110.8O1—C13—H13A109.5
H6A—C6—H6B108.9O1—C13—H13B109.5
N1—C1—C28111.39 (12)H13A—C13—H13B109.5
N1—C1—C22112.55 (11)O1—C13—H13C109.5
C28—C1—C22100.97 (12)H13A—C13—H13C109.5
N1—C1—C2101.48 (11)H13B—C13—H13C109.5
C28—C1—C2118.10 (11)C16—C17—C18121.3 (2)
C22—C1—C2112.82 (11)C16—C17—H17119.3
C24—C23—C28122.04 (15)C18—C17—H17119.3
C24—C23—N2128.50 (15)
C4—C3—C7—C12165.30 (15)C3—C2—C1—N15.61 (13)
C2—C3—C7—C1272.33 (18)C14—C2—C1—C28108.88 (15)
C4—C3—C7—C812.5 (2)C21—C2—C1—C287.29 (18)
C2—C3—C7—C8109.86 (17)C3—C2—C1—C28127.65 (13)
C5—N1—C4—C654.57 (15)C14—C2—C1—C228.42 (17)
C1—N1—C4—C6171.95 (11)C21—C2—C1—C22124.59 (13)
C5—N1—C4—C3178.25 (12)C3—C2—C1—C22115.05 (13)
C1—N1—C4—C348.27 (14)C27—C28—C23—C242.8 (2)
C7—C3—C4—N1169.57 (12)C1—C28—C23—C24179.96 (14)
C2—C3—C4—N140.95 (13)C27—C28—C23—N2175.20 (14)
C7—C3—C4—C678.07 (17)C1—C28—C23—N21.96 (17)
C2—C3—C4—C6153.31 (13)C22—N2—C23—C24177.76 (16)
O3—C21—C2—C14138.12 (15)C22—N2—C23—C280.08 (18)
C20—C21—C2—C1442.31 (16)O3—C21—C20—C15171.66 (16)
O3—C21—C2—C315.4 (2)C2—C21—C20—C158.8 (2)
C20—C21—C2—C3165.02 (13)O3—C21—C20—C1914.3 (2)
O3—C21—C2—C1100.34 (17)C2—C21—C20—C19165.29 (15)
C20—C21—C2—C179.23 (16)C1—N1—C5—S1170.89 (10)
C7—C3—C2—C1428.19 (17)C4—N1—C5—S143.24 (13)
C4—C3—C2—C14101.49 (14)C6—S1—C5—N115.87 (11)
C7—C3—C2—C2189.17 (14)C23—C28—C27—C262.2 (2)
C4—C3—C2—C21141.15 (12)C1—C28—C27—C26178.71 (15)
C7—C3—C2—C1151.46 (11)C14—O2—C15—C2012.9 (2)
C4—C3—C2—C121.77 (13)C14—O2—C15—C16167.10 (14)
C15—O2—C14—C251.93 (18)C19—C20—C15—O2176.85 (15)
C21—C2—C14—O264.87 (15)C21—C20—C15—O29.0 (2)
C3—C2—C14—O2173.35 (12)C19—C20—C15—C163.2 (2)
C1—C2—C14—O254.96 (17)C21—C20—C15—C16171.00 (15)
C23—N2—C22—O4173.97 (15)C13—O1—C10—C111.3 (3)
C23—N2—C22—C12.00 (17)C13—O1—C10—C9179.4 (2)
N1—C4—C6—S137.67 (13)C12—C11—C10—O1179.71 (18)
C3—C4—C6—S1147.90 (11)C12—C11—C10—C90.5 (3)
C5—S1—C6—C412.63 (11)C8—C7—C12—C111.5 (3)
C5—N1—C1—C2871.78 (16)C3—C7—C12—C11179.45 (16)
C4—N1—C1—C28160.10 (11)C10—C11—C12—C71.3 (3)
C5—N1—C1—C2240.80 (17)C28—C23—C24—C251.6 (2)
C4—N1—C1—C2287.32 (14)N2—C23—C24—C25175.98 (16)
C5—N1—C1—C2161.65 (12)C12—C7—C8—C90.1 (3)
C4—N1—C1—C233.53 (13)C3—C7—C8—C9177.75 (17)
C27—C28—C1—N154.2 (2)C23—C24—C25—C260.0 (3)
C23—C28—C1—N1122.59 (13)C7—C8—C9—C101.9 (3)
C27—C28—C1—C22173.88 (16)O1—C10—C9—C8178.66 (17)
C23—C28—C1—C222.89 (15)C11—C10—C9—C82.1 (3)
C27—C28—C1—C262.7 (2)C24—C25—C26—C270.5 (3)
C23—C28—C1—C2120.57 (14)C28—C27—C26—C250.6 (3)
O4—C22—C1—N154.2 (2)O2—C15—C16—C17178.24 (17)
N2—C22—C1—N1121.79 (14)C20—C15—C16—C171.8 (3)
O4—C22—C1—C28173.07 (15)C15—C20—C19—C182.0 (3)
N2—C22—C1—C282.93 (15)C21—C20—C19—C18172.15 (18)
O4—C22—C1—C259.9 (2)C20—C19—C18—C170.5 (3)
N2—C22—C1—C2124.09 (13)C15—C16—C17—C180.8 (3)
C14—C2—C1—N1129.09 (13)C19—C18—C17—C162.0 (3)
C21—C2—C1—N1114.74 (13)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
N2—H2···O4i0.862.132.949 (2)160
C9—H9···O3ii0.932.423.312 (2)160
Symmetry codes: (i) x, y, z; (ii) x+1, y1/2, z+1/2.
 

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