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The crystal packing of the title compound {systematic name: 3-[(2,3-dioxo-3-pyrrolin-1-yl)acet­yl]-2-[2-(4-methoxy­phen­yl)vin­yl]-2,3-dihydro-1,3-benzothia­zole}, C28H22N2O4S, is stabil­ized by inter­molecular C—H...O and C—H...S hydrogen bonds and by π–π stacking inter­actions occurring between a benzene ring and the pyrrole ring of centrosymmetrically related mol­ecules.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536806050082/rz2077sup1.cif
Contains datablocks global, I

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S1600536806050082/rz2077Isup2.hkl
Contains datablock I

CCDC reference: 630220

Key indicators

  • Single-crystal X-ray study
  • T = 273 K
  • Mean [sigma](C-C) = 0.003 Å
  • R factor = 0.039
  • wR factor = 0.102
  • Data-to-parameter ratio = 13.4

checkCIF/PLATON results

No syntax errors found



Alert level C PLAT066_ALERT_1_C Predicted and Reported Transmissions Identical . ? PLAT220_ALERT_2_C Large Non-Solvent C Ueq(max)/Ueq(min) ... 3.03 Ratio PLAT222_ALERT_3_C Large Non-Solvent H Ueq(max)/Ueq(min) ... 3.28 Ratio PLAT230_ALERT_2_C Hirshfeld Test Diff for C5 - C6 .. 5.53 su
0 ALERT level A = In general: serious problem 0 ALERT level B = Potentially serious problem 4 ALERT level C = Check and explain 0 ALERT level G = General alerts; check 1 ALERT type 1 CIF construction/syntax error, inconsistent or missing data 2 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 0 ALERT type 5 Informative message, check

Computing details top

Data collection: SMART (Bruker, 1997); cell refinement: SAINT (Bruker, 1997); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: SHELXTL (Bruker, 1997); software used to prepare material for publication: SHELXTL.

(I) top
Crystal data top
C28H22N2O4SF(000) = 1008
Mr = 482.54Dx = 1.321 Mg m3
Monoclinic, P21/nMo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ynCell parameters from 2910 reflections
a = 9.970 (5) Åθ = 2.2–21.9°
b = 10.191 (5) ŵ = 0.17 mm1
c = 23.941 (11) ÅT = 273 K
β = 94.310 (7)°Block, colourless
V = 2426 (2) Å30.28 × 0.22 × 0.16 mm
Z = 4
Data collection top
APEX II CCD area detector
diffractometer
4258 independent reflections
Radiation source: fine-focus sealed tube3012 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.025
φ and ω scansθmax = 25.0°, θmin = 2.2°
Absorption correction: multi-scan
(SADABS; Sheldrick, 1996)
h = 1110
Tmin = 0.952, Tmax = 0.973k = 1211
12808 measured reflectionsl = 2828
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)] = 0.039Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.102H-atom parameters constrained
S = 1.03 w = 1/[σ2(Fo2) + (0.0413P)2 + 0.6152P]
where P = (Fo2 + 2Fc2)/3
4258 reflections(Δ/σ)max < 0.001
317 parametersΔρmax = 0.34 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
S10.47726 (6)0.51328 (5)0.08892 (2)0.06071 (18)
O10.04815 (19)0.11811 (18)0.14953 (8)0.0970 (6)
O20.48525 (19)0.12135 (15)0.20196 (7)0.0830 (5)
O30.8038 (2)0.01662 (18)0.21663 (8)0.1049 (7)
O40.4564 (2)0.16266 (18)0.11186 (9)0.0962 (6)
N10.47664 (15)0.27929 (14)0.13590 (6)0.0415 (4)
N20.63509 (18)0.04743 (15)0.15230 (7)0.0549 (4)
C10.1723 (2)0.0603 (2)0.02253 (9)0.0592 (6)
H10.19470.00570.00330.071*
C20.0798 (2)0.0340 (2)0.06707 (9)0.0645 (6)
H20.04220.04930.07140.077*
C280.1074 (4)0.0070 (3)0.15874 (14)0.1269 (13)
H29A0.03830.07090.16330.190*
H29B0.16760.00460.19200.190*
H29C0.15660.03040.12720.190*
C40.1032 (2)0.2537 (2)0.09825 (10)0.0678 (6)
H40.08050.32020.12380.081*
C50.1955 (2)0.2770 (2)0.05411 (9)0.0598 (6)
H50.23450.35970.05010.072*
C60.2320 (2)0.1809 (2)0.01541 (8)0.0504 (5)
C70.3290 (2)0.2061 (2)0.03326 (8)0.0530 (5)
H70.31810.15940.06600.064*
C80.42845 (19)0.2891 (2)0.03347 (7)0.0487 (5)
H80.44640.32330.00120.058*
C90.51688 (19)0.33594 (17)0.08219 (7)0.0420 (4)
C100.66753 (19)0.33310 (17)0.07491 (8)0.0457 (5)
C110.7171 (2)0.2987 (2)0.02465 (9)0.0589 (6)
H110.65870.27030.00500.071*
C120.8543 (3)0.3064 (3)0.01840 (14)0.0877 (9)
H120.88700.28430.01570.105*
C130.9413 (3)0.3460 (3)0.0616 (2)0.1043 (11)
H131.03300.35110.05710.125*
C140.8931 (3)0.3781 (3)0.11135 (16)0.0920 (9)
H140.95270.40300.14120.110*
C150.7569 (2)0.3745 (2)0.11843 (10)0.0654 (6)
H150.72530.39980.15240.078*
C160.3576 (2)0.47935 (18)0.13649 (8)0.0486 (5)
C170.2615 (2)0.5654 (2)0.15317 (9)0.0590 (5)
H170.25330.64890.13770.071*
C180.1779 (2)0.5255 (2)0.19318 (9)0.0627 (6)
H180.11330.58260.20520.075*
C190.1901 (2)0.4021 (3)0.21515 (8)0.0643 (6)
H190.13250.37620.24190.077*
C200.2860 (2)0.3139 (2)0.19868 (8)0.0556 (5)
H200.29250.23010.21400.067*
C210.37187 (19)0.35372 (17)0.15892 (7)0.0435 (4)
C220.5196 (2)0.16048 (18)0.15752 (8)0.0507 (5)
C230.6122 (2)0.07637 (19)0.12467 (9)0.0577 (5)
H23A0.57160.06210.08710.069*
H23B0.69720.12130.12190.069*
C240.7253 (3)0.0644 (2)0.19840 (10)0.0711 (7)
C250.7005 (3)0.1992 (2)0.21900 (10)0.0865 (9)
H250.74960.24040.24860.104*
C260.5996 (3)0.2501 (2)0.18928 (11)0.0825 (8)
H260.56460.33350.19420.099*
C270.5491 (3)0.1543 (2)0.14641 (10)0.0643 (6)
C30.0437 (2)0.1318 (2)0.10499 (9)0.0640 (6)
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
S10.0722 (4)0.0390 (3)0.0734 (4)0.0045 (3)0.0218 (3)0.0143 (3)
O10.0944 (14)0.0924 (13)0.0966 (13)0.0170 (11)0.0435 (11)0.0115 (10)
O20.1232 (15)0.0665 (10)0.0646 (10)0.0271 (10)0.0410 (10)0.0300 (8)
O30.1215 (17)0.0706 (12)0.1156 (15)0.0017 (11)0.0367 (12)0.0219 (11)
O40.0954 (14)0.0831 (13)0.1070 (14)0.0198 (11)0.0139 (12)0.0003 (11)
N10.0526 (10)0.0365 (8)0.0363 (8)0.0007 (7)0.0088 (7)0.0040 (6)
N20.0735 (12)0.0339 (9)0.0569 (10)0.0013 (8)0.0027 (9)0.0047 (7)
C10.0666 (15)0.0544 (13)0.0554 (13)0.0023 (11)0.0029 (11)0.0071 (10)
C20.0678 (15)0.0555 (13)0.0687 (14)0.0148 (11)0.0041 (12)0.0014 (11)
C280.135 (3)0.119 (3)0.117 (2)0.060 (2)0.058 (2)0.011 (2)
C40.0684 (15)0.0605 (14)0.0724 (15)0.0007 (12)0.0083 (12)0.0171 (12)
C50.0570 (14)0.0518 (12)0.0706 (14)0.0096 (10)0.0039 (11)0.0021 (11)
C60.0462 (12)0.0539 (12)0.0511 (12)0.0009 (9)0.0033 (9)0.0014 (10)
C70.0577 (13)0.0540 (12)0.0479 (12)0.0002 (10)0.0091 (10)0.0043 (9)
C80.0477 (12)0.0611 (12)0.0381 (10)0.0017 (10)0.0084 (9)0.0074 (9)
C90.0491 (11)0.0379 (10)0.0394 (10)0.0004 (8)0.0061 (8)0.0076 (8)
C100.0458 (11)0.0360 (10)0.0552 (12)0.0034 (8)0.0025 (9)0.0128 (9)
C110.0548 (14)0.0572 (13)0.0665 (14)0.0039 (11)0.0167 (11)0.0129 (11)
C120.0691 (19)0.0753 (17)0.125 (2)0.0117 (15)0.0455 (18)0.0233 (17)
C130.0487 (18)0.0738 (19)0.192 (4)0.0009 (14)0.019 (2)0.031 (2)
C140.0562 (18)0.0673 (17)0.147 (3)0.0136 (14)0.0297 (18)0.0204 (18)
C150.0633 (15)0.0522 (12)0.0779 (15)0.0096 (11)0.0130 (12)0.0086 (11)
C160.0519 (12)0.0440 (11)0.0502 (11)0.0004 (9)0.0047 (9)0.0028 (9)
C170.0605 (14)0.0497 (12)0.0663 (14)0.0052 (11)0.0015 (11)0.0108 (10)
C180.0535 (13)0.0775 (16)0.0565 (13)0.0092 (12)0.0001 (11)0.0225 (12)
C190.0545 (14)0.0938 (18)0.0457 (12)0.0017 (13)0.0108 (10)0.0062 (12)
C200.0587 (13)0.0648 (13)0.0438 (11)0.0039 (11)0.0072 (10)0.0035 (10)
C210.0499 (12)0.0446 (11)0.0358 (10)0.0027 (9)0.0024 (8)0.0041 (8)
C220.0677 (14)0.0397 (11)0.0455 (11)0.0009 (9)0.0094 (10)0.0074 (9)
C230.0761 (15)0.0391 (11)0.0593 (13)0.0072 (10)0.0136 (11)0.0122 (9)
C240.103 (2)0.0439 (12)0.0641 (15)0.0086 (13)0.0070 (14)0.0095 (11)
C250.153 (3)0.0476 (14)0.0567 (14)0.0227 (16)0.0066 (16)0.0059 (11)
C260.140 (3)0.0393 (12)0.0700 (16)0.0032 (14)0.0168 (17)0.0043 (12)
C270.0863 (19)0.0437 (12)0.0640 (15)0.0036 (12)0.0122 (13)0.0022 (11)
C30.0543 (14)0.0732 (15)0.0622 (14)0.0031 (12)0.0110 (11)0.0022 (12)
Geometric parameters (Å, º) top
S1—C161.745 (2)C9—C101.525 (3)
S1—C91.859 (2)C10—C111.380 (3)
O1—C31.360 (3)C10—C151.385 (3)
O1—C281.416 (3)C11—C121.390 (3)
O2—C221.210 (2)C11—H110.9300
O3—C241.197 (3)C12—C131.360 (4)
O4—C271.197 (3)C12—H120.9300
N1—C221.373 (2)C13—C141.358 (4)
N1—C211.434 (2)C13—H130.9300
N1—C91.492 (2)C14—C151.381 (4)
N2—C241.381 (3)C14—H140.9300
N2—C271.386 (3)C15—H150.9300
N2—C231.435 (2)C16—C171.380 (3)
C1—C61.370 (3)C16—C211.392 (3)
C1—C21.383 (3)C17—C181.377 (3)
C1—H10.9300C17—H170.9300
C2—C31.378 (3)C18—C191.365 (3)
C2—H20.9300C18—H180.9300
C28—H29A0.9600C19—C201.391 (3)
C28—H29B0.9600C19—H190.9300
C28—H29C0.9600C20—C211.388 (3)
C4—C51.369 (3)C20—H200.9300
C4—C31.381 (3)C22—C231.521 (3)
C4—H40.9300C23—H23A0.9700
C5—C61.378 (3)C23—H23B0.9700
C5—H50.9300C24—C251.486 (3)
C6—C71.479 (3)C25—C261.296 (4)
C7—C81.303 (3)C25—H250.9300
C7—H70.9300C26—C271.477 (3)
C8—C91.487 (3)C26—H260.9300
C8—H80.9300
C16—S1—C991.38 (9)C14—C13—H13120.3
C3—O1—C28117.6 (2)C12—C13—H13120.3
C22—N1—C21122.52 (15)C13—C14—C15121.2 (3)
C22—N1—C9124.73 (15)C13—C14—H14119.4
C21—N1—C9112.17 (14)C15—C14—H14119.4
C24—N2—C27110.08 (19)C14—C15—C10119.9 (3)
C24—N2—C23123.37 (18)C14—C15—H15120.0
C27—N2—C23124.61 (19)C10—C15—H15120.0
C6—C1—C2121.9 (2)C17—C16—C21121.73 (19)
C6—C1—H1119.1C17—C16—S1125.93 (16)
C2—C1—H1119.1C21—C16—S1112.29 (14)
C3—C2—C1119.6 (2)C18—C17—C16118.9 (2)
C3—C2—H2120.2C18—C17—H17120.6
C1—C2—H2120.2C16—C17—H17120.6
O1—C28—H29A109.5C19—C18—C17119.9 (2)
O1—C28—H29B109.5C19—C18—H18120.0
H29A—C28—H29B109.5C17—C18—H18120.0
O1—C28—H29C109.5C18—C19—C20121.9 (2)
H29A—C28—H29C109.5C18—C19—H19119.0
H29B—C28—H29C109.5C20—C19—H19119.0
C5—C4—C3120.3 (2)C21—C20—C19118.6 (2)
C5—C4—H4119.9C21—C20—H20120.7
C3—C4—H4119.9C19—C20—H20120.7
C4—C5—C6121.6 (2)C20—C21—C16118.91 (18)
C4—C5—H5119.2C20—C21—N1127.85 (17)
C6—C5—H5119.2C16—C21—N1113.24 (16)
C1—C6—C5117.60 (19)O2—C22—N1121.41 (18)
C1—C6—C7120.37 (18)O2—C22—C23119.47 (17)
C5—C6—C7122.01 (19)N1—C22—C23119.11 (16)
C8—C7—C6124.59 (19)N2—C23—C22109.80 (17)
C8—C7—H7117.7N2—C23—H23A109.7
C6—C7—H7117.7C22—C23—H23A109.7
C7—C8—C9128.15 (18)N2—C23—H23B109.7
C7—C8—H8115.9C22—C23—H23B109.7
C9—C8—H8115.9H23A—C23—H23B108.2
C8—C9—N1111.70 (15)O3—C24—N2125.0 (2)
C8—C9—C10115.80 (15)O3—C24—C25129.5 (2)
N1—C9—C10114.97 (14)N2—C24—C25105.4 (2)
C8—C9—S1105.24 (13)C26—C25—C24109.2 (2)
N1—C9—S1103.22 (11)C26—C25—H25125.4
C10—C9—S1104.23 (12)C24—C25—H25125.4
C11—C10—C15118.8 (2)C25—C26—C27109.1 (2)
C11—C10—C9121.64 (18)C25—C26—H26125.5
C15—C10—C9119.45 (19)C27—C26—H26125.5
C10—C11—C12120.0 (2)O4—C27—N2124.5 (2)
C10—C11—H11120.0O4—C27—C26129.7 (2)
C12—C11—H11120.0N2—C27—C26105.8 (2)
C13—C12—C11120.8 (3)O1—C3—C2124.7 (2)
C13—C12—H12119.6O1—C3—C4116.2 (2)
C11—C12—H12119.6C2—C3—C4119.0 (2)
C14—C13—C12119.4 (3)
C6—C1—C2—C31.4 (3)C17—C18—C19—C200.5 (3)
C3—C4—C5—C60.1 (4)C18—C19—C20—C210.3 (3)
C2—C1—C6—C50.7 (3)C19—C20—C21—C160.9 (3)
C2—C1—C6—C7179.0 (2)C19—C20—C21—N1179.64 (18)
C4—C5—C6—C10.1 (3)C17—C16—C21—C200.7 (3)
C4—C5—C6—C7178.4 (2)S1—C16—C21—C20178.20 (14)
C1—C6—C7—C8150.6 (2)C17—C16—C21—N1179.61 (17)
C5—C6—C7—C831.2 (3)S1—C16—C21—N12.9 (2)
C6—C7—C8—C9169.52 (18)C22—N1—C21—C2010.3 (3)
C7—C8—C9—N12.1 (3)C9—N1—C21—C20161.29 (18)
C7—C8—C9—C10132.0 (2)C22—N1—C21—C16170.83 (17)
C7—C8—C9—S1113.5 (2)C9—N1—C21—C1617.5 (2)
C22—N1—C9—C886.4 (2)C21—N1—C22—O211.0 (3)
C21—N1—C9—C885.05 (18)C9—N1—C22—O2178.48 (19)
C22—N1—C9—C1048.2 (2)C21—N1—C22—C23168.87 (17)
C21—N1—C9—C10140.37 (15)C9—N1—C22—C231.7 (3)
C22—N1—C9—S1161.04 (15)C24—N2—C23—C2279.4 (3)
C21—N1—C9—S127.54 (16)C27—N2—C23—C2283.2 (2)
C16—S1—C9—C892.84 (14)O2—C22—C23—N24.8 (3)
C16—S1—C9—N124.40 (13)N1—C22—C23—N2175.05 (17)
C16—S1—C9—C10144.85 (13)C27—N2—C24—O3173.2 (3)
C8—C9—C10—C114.8 (2)C23—N2—C24—O38.5 (4)
N1—C9—C10—C11137.50 (18)C27—N2—C24—C255.9 (3)
S1—C9—C10—C11110.27 (17)C23—N2—C24—C25170.7 (2)
C8—C9—C10—C15179.65 (17)O3—C24—C25—C26175.4 (3)
N1—C9—C10—C1547.0 (2)N2—C24—C25—C263.7 (3)
S1—C9—C10—C1565.27 (18)C24—C25—C26—C270.2 (3)
C15—C10—C11—C120.2 (3)C24—N2—C27—O4175.8 (2)
C9—C10—C11—C12175.32 (18)C23—N2—C27—O411.2 (4)
C10—C11—C12—C130.9 (4)C24—N2—C27—C265.8 (2)
C11—C12—C13—C140.1 (4)C23—N2—C27—C26170.36 (19)
C12—C13—C14—C151.7 (4)C25—C26—C27—O4178.3 (3)
C13—C14—C15—C102.3 (4)C25—C26—C27—N23.4 (3)
C11—C10—C15—C141.3 (3)C28—O1—C3—C22.4 (4)
C9—C10—C15—C14176.97 (19)C28—O1—C3—C4177.8 (3)
C9—S1—C16—C17165.92 (18)C1—C2—C3—O1178.5 (2)
C9—S1—C16—C2116.67 (15)C1—C2—C3—C41.4 (4)
C21—C16—C17—C180.1 (3)C5—C4—C3—O1179.1 (2)
S1—C16—C17—C18177.03 (16)C5—C4—C3—C20.7 (4)
C16—C17—C18—C190.7 (3)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
C7—H7···N10.932.532.867 (3)102
C20—H20···O20.932.262.789 (3)116
C8—H8···S1i0.932.833.734 (2)165
C18—H18···O2ii0.932.533.243 (3)134
Symmetry codes: (i) x+1, y+1, z; (ii) x+1/2, y+1/2, z+1/2.
 

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