Download citation
Download citation
link to html
The title compound, C12H12BrNO4S, belongs to the class of substituted thia­zolidine-2,4-diones. Compounds of this type are important starting materials in pharmaceutical chemistry. The thia­zolidine-2,4-dione ring is disordered about a twofold rotation axis. Geometric parameters, other than those of the disordered groups, are in the normal ranges.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536805004137/nc6020sup1.cif
Contains datablocks I, global

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S1600536805004137/nc6020Isup2.hkl
Contains datablock I

CCDC reference: 269820

Key indicators

  • Single-crystal X-ray study
  • T = 173 K
  • Mean [sigma](C-C) = 0.004 Å
  • R factor = 0.032
  • wR factor = 0.078
  • Data-to-parameter ratio = 12.2

checkCIF/PLATON results

No syntax errors found



Alert level B PLAT431_ALERT_2_B Short Inter HL..A Contact Br12 .. O1 .. 3.06 Ang.
Alert level C PLAT125_ALERT_4_C No _symmetry_space_group_name_Hall Given ....... ? PLAT241_ALERT_2_C Check High Ueq as Compared to Neighbors for S1' PLAT242_ALERT_2_C Check Low Ueq as Compared to Neighbors for C3' PLAT301_ALERT_3_C Main Residue Disorder ......................... 24.00 Perc. PLAT431_ALERT_2_C Short Inter HL..A Contact Br12 .. O1' .. 3.07 Ang. PLAT432_ALERT_2_C Short Inter X...Y Contact O1 .. C3 .. 2.98 Ang. PLAT779_ALERT_2_C Suspect or Irrelevant (Bond) Angle in CIF ...... 15.00 Deg. C1' -N1 -C1 1.555 1.555 1.555 PLAT779_ALERT_2_C Suspect or Irrelevant (Bond) Angle in CIF ...... 23.40 Deg. C3 -N1 -C3' 1.555 1.555 1.555
0 ALERT level A = In general: serious problem 1 ALERT level B = Potentially serious problem 8 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 7 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: X-AREA (Stoe & Cie, 2001); cell refinement: X-AREA; data reduction: X-AREA; program(s) used to solve structure: SHELXS97 (Sheldrick, 1990); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: XP in SHELXTL-Plus (Sheldrick, 1991); software used to prepare material for publication: SHELXL97 and PLATON (Spek, 2003).

3-(2-Bromo-4,5-dimethoxybenzyl)thiazolidine-2,4-dione top
Crystal data top
C12H12BrNO4SF(000) = 696
Mr = 346.20Dx = 1.722 Mg m3
Monoclinic, P21/cMo Kα radiation, λ = 0.71073 Å
a = 8.6677 (10) ÅCell parameters from 7895 reflections
b = 18.5082 (18) Åθ = 4.2–25.6°
c = 8.9746 (10) ŵ = 3.24 mm1
β = 111.950 (9)°T = 173 K
V = 1335.4 (3) Å3Block, colourless
Z = 40.36 × 0.32 × 0.29 mm
Data collection top
Stoe IPDS-II two-circle
diffractometer
2486 independent reflections
Radiation source: fine-focus sealed tube2242 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.023
ω scansθmax = 25.7°, θmin = 4.1°
Absorption correction: multi-scan
(MULABS; Spek, 2003; Blessing, 1995)
h = 910
Tmin = 0.334, Tmax = 0.390k = 1922
6240 measured reflectionsl = 1010
Refinement top
Refinement on F2Secondary atom site location: difference Fourier map
Least-squares matrix: fullHydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.032H-atom parameters constrained
wR(F2) = 0.078 w = 1/[σ2(Fo2) + (0.0441P)2 + 0.5152P]
where P = (Fo2 + 2Fc2)/3
S = 1.16(Δ/σ)max = 0.002
2486 reflectionsΔρmax = 0.46 e Å3
203 parametersΔρmin = 0.79 e Å3
0 restraintsExtinction correction: SHELXL97, Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4
Primary atom site location: structure-invariant direct methodsExtinction coefficient: 0.0107 (12)
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*/UeqOcc. (<1)
Br121.19325 (3)0.303132 (15)0.54646 (3)0.03067 (13)
N10.7355 (3)0.20765 (11)0.5607 (2)0.0246 (5)
S10.43745 (16)0.14830 (6)0.49017 (12)0.0330 (4)0.740 (5)
C10.5834 (6)0.2152 (3)0.5919 (6)0.0185 (10)0.740 (5)
O10.5615 (4)0.2613 (2)0.6783 (4)0.0268 (8)0.740 (5)
C20.5764 (9)0.1064 (4)0.4080 (9)0.0324 (15)0.740 (5)
H2A0.59700.05650.44300.039*0.740 (5)
H2B0.52790.10720.29150.039*0.740 (5)
C30.7378 (7)0.14906 (19)0.4682 (4)0.0218 (8)0.740 (5)
O20.8605 (6)0.13352 (17)0.4383 (4)0.0355 (9)0.740 (5)
S1'0.6378 (10)0.0908 (3)0.3956 (7)0.062 (2)0.260 (5)
C1'0.598 (2)0.2004 (9)0.563 (2)0.022 (4)*0.260 (5)
O1'0.5488 (18)0.2454 (9)0.6348 (16)0.030 (3)*0.260 (5)
C2'0.509 (3)0.1371 (8)0.4654 (18)0.043 (3)*0.260 (5)
H2C0.41260.15380.37560.051*0.260 (5)
H2D0.47130.10540.53070.051*0.260 (5)
C3'0.816 (2)0.1494 (9)0.4786 (19)0.031 (4)*0.260 (5)
O2'0.9434 (18)0.1456 (7)0.4835 (16)0.058 (4)*0.260 (5)
O410.7846 (2)0.51026 (10)0.2317 (2)0.0271 (4)
O510.5405 (2)0.46597 (11)0.3110 (2)0.0306 (4)
C40.8696 (3)0.26039 (14)0.6299 (3)0.0246 (5)
H4A0.97560.23690.65030.029*
H4B0.86870.27700.73210.029*
C110.8541 (3)0.32519 (13)0.5213 (3)0.0200 (5)
C120.9815 (3)0.34997 (14)0.4763 (3)0.0209 (5)
C130.9635 (3)0.41147 (13)0.3805 (3)0.0220 (5)
H131.05170.42670.35310.026*
C140.8154 (3)0.44994 (13)0.3259 (3)0.0206 (5)
C150.6829 (3)0.42572 (13)0.3701 (3)0.0210 (5)
C160.7054 (3)0.36535 (14)0.4664 (3)0.0226 (5)
H160.61850.35060.49630.027*
C420.9181 (4)0.53475 (16)0.1850 (3)0.0314 (6)
H42A1.01400.54560.27930.047*
H42B0.88360.57740.12000.047*
H42C0.94560.49750.12460.047*
C520.3979 (4)0.43841 (18)0.3373 (4)0.0382 (7)
H52A0.37140.39110.29070.057*
H52B0.30500.47010.28820.057*
H52C0.42210.43560.45060.057*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
Br120.01665 (17)0.03972 (19)0.03410 (18)0.00527 (11)0.00770 (11)0.00516 (11)
N10.0353 (13)0.0208 (11)0.0171 (9)0.0012 (9)0.0090 (9)0.0013 (7)
S10.0307 (7)0.0365 (6)0.0297 (5)0.0097 (4)0.0088 (4)0.0036 (4)
C10.028 (2)0.015 (2)0.0118 (19)0.0012 (17)0.0062 (17)0.0038 (17)
O10.0257 (16)0.034 (2)0.0233 (16)0.0021 (13)0.0118 (13)0.0065 (15)
C20.043 (3)0.022 (3)0.028 (3)0.005 (2)0.009 (2)0.001 (2)
C30.034 (3)0.0177 (18)0.0182 (16)0.0077 (16)0.0150 (16)0.0067 (12)
O20.049 (3)0.0315 (16)0.0351 (16)0.0164 (17)0.0260 (18)0.0023 (13)
S1'0.111 (6)0.025 (3)0.0298 (19)0.012 (3)0.001 (3)0.0006 (16)
O410.0250 (10)0.0261 (9)0.0335 (9)0.0000 (8)0.0148 (8)0.0075 (7)
O510.0228 (10)0.0324 (10)0.0416 (10)0.0084 (8)0.0179 (8)0.0138 (8)
C40.0194 (12)0.0315 (14)0.0218 (11)0.0044 (10)0.0064 (9)0.0057 (10)
C110.0198 (12)0.0225 (12)0.0180 (10)0.0004 (9)0.0075 (9)0.0020 (9)
C120.0153 (11)0.0278 (13)0.0185 (10)0.0013 (9)0.0050 (9)0.0063 (9)
C130.0190 (12)0.0268 (13)0.0223 (11)0.0045 (10)0.0103 (9)0.0033 (9)
C140.0224 (13)0.0199 (12)0.0197 (11)0.0029 (9)0.0079 (9)0.0021 (9)
C150.0191 (12)0.0232 (12)0.0213 (11)0.0027 (10)0.0083 (9)0.0010 (9)
C160.0203 (12)0.0262 (13)0.0242 (11)0.0004 (10)0.0116 (9)0.0012 (9)
C420.0314 (15)0.0311 (14)0.0359 (14)0.0038 (12)0.0174 (12)0.0062 (11)
C520.0246 (15)0.0452 (17)0.0521 (17)0.0104 (13)0.0229 (13)0.0151 (14)
Geometric parameters (Å, º) top
Br12—C121.911 (2)O41—C421.443 (3)
N1—C1'1.206 (18)O51—C151.368 (3)
N1—C31.371 (4)O51—C521.435 (3)
N1—C11.453 (6)C4—C111.519 (3)
N1—C41.466 (3)C4—H4A0.9700
N1—C3'1.60 (2)C4—H4B0.9700
S1—C11.762 (5)C11—C121.388 (3)
S1—C21.806 (6)C11—C161.408 (3)
C1—O11.215 (8)C12—C131.400 (4)
C2—C31.519 (9)C13—C141.387 (3)
C2—H2A0.9700C13—H130.9300
C2—H2B0.9700C14—C151.420 (3)
C3—O21.224 (6)C15—C161.381 (3)
S1'—C2'1.70 (2)C16—H160.9300
S1'—C3'1.802 (18)C42—H42A0.9600
C1'—O1'1.221 (19)C42—H42B0.9600
C1'—C2'1.50 (2)C42—H42C0.9600
C2'—H2C0.9700C52—H52A0.9600
C2'—H2D0.9700C52—H52B0.9600
C3'—O2'1.09 (2)C52—H52C0.9600
O41—C141.365 (3)
C1'—N1—C399.4 (9)C15—O51—C52116.8 (2)
C1'—N1—C115.0 (8)N1—C4—C11112.82 (19)
C3—N1—C1114.4 (4)N1—C4—H4A109.0
C1'—N1—C4134.2 (8)C11—C4—H4A109.0
C3—N1—C4126.5 (3)N1—C4—H4B109.0
C1—N1—C4119.2 (3)C11—C4—H4B109.0
C1'—N1—C3'122.3 (10)H4A—C4—H4B107.8
C3—N1—C3'23.4 (5)C12—C11—C16116.6 (2)
C1—N1—C3'137.1 (7)C12—C11—C4123.9 (2)
C4—N1—C3'103.4 (6)C16—C11—C4119.4 (2)
C1—S1—C293.1 (3)C11—C12—C13122.0 (2)
O1—C1—N1124.0 (4)C11—C12—Br12121.66 (19)
O1—C1—S1124.8 (5)C13—C12—Br12116.37 (18)
N1—C1—S1111.1 (4)C14—C13—C12120.7 (2)
C3—C2—S1107.3 (4)C14—C13—H13119.7
C3—C2—H2A110.3C12—C13—H13119.7
S1—C2—H2A110.3O41—C14—C13125.4 (2)
C3—C2—H2B110.3O41—C14—C15116.1 (2)
S1—C2—H2B110.3C13—C14—C15118.5 (2)
H2A—C2—H2B108.5O51—C15—C16125.4 (2)
O2—C3—N1122.0 (5)O51—C15—C14115.3 (2)
O2—C3—C2124.0 (4)C16—C15—C14119.4 (2)
N1—C3—C2114.0 (4)C15—C16—C11122.9 (2)
C2'—S1'—C3'97.0 (9)C15—C16—H16118.6
N1—C1'—O1'118.5 (17)C11—C16—H16118.6
N1—C1'—C2'111.8 (14)O41—C42—H42A109.5
O1'—C1'—C2'129.6 (18)O41—C42—H42B109.5
C1'—C2'—S1'110.3 (14)H42A—C42—H42B109.5
C1'—C2'—H2C109.6O41—C42—H42C109.5
S1'—C2'—H2C109.6H42A—C42—H42C109.5
C1'—C2'—H2D109.6H42B—C42—H42C109.5
S1'—C2'—H2D109.6O51—C52—H52A109.5
H2C—C2'—H2D108.1O51—C52—H52B109.5
O2'—C3'—N1129.0 (14)H52A—C52—H52B109.5
O2'—C3'—S1'132.5 (17)O51—C52—H52C109.5
N1—C3'—S1'98.3 (11)H52A—C52—H52C109.5
C14—O41—C42116.4 (2)H52B—C52—H52C109.5
C1'—N1—C1—O1180 (4)C1—N1—C3'—O2'166.8 (13)
C3—N1—C1—O1175.9 (4)C4—N1—C3'—O2'6.3 (17)
C4—N1—C1—O13.2 (5)C1'—N1—C3'—S1'5.2 (13)
C3'—N1—C1—O1169.1 (8)C3—N1—C3'—S1'7.2 (8)
C1'—N1—C1—S11 (3)C1—N1—C3'—S1'8.5 (11)
C3—N1—C1—S13.4 (3)C4—N1—C3'—S1'178.4 (5)
C4—N1—C1—S1177.52 (19)C2'—S1'—C3'—O2'173.9 (17)
C3'—N1—C1—S110.2 (9)C2'—S1'—C3'—N11.1 (8)
C2—S1—C1—O1177.6 (4)C1'—N1—C4—C1188.1 (11)
C2—S1—C1—N11.7 (3)C3—N1—C4—C1191.8 (3)
C1—S1—C2—C30.2 (4)C1—N1—C4—C1189.2 (3)
C1'—N1—C3—O2177.4 (8)C3'—N1—C4—C1196.2 (6)
C1—N1—C3—O2176.4 (3)N1—C4—C11—C12128.1 (2)
C4—N1—C3—O22.6 (5)N1—C4—C11—C1654.6 (3)
C3'—N1—C3—O28.1 (13)C16—C11—C12—C130.4 (3)
C1'—N1—C3—C22.6 (9)C4—C11—C12—C13177.7 (2)
C1—N1—C3—C23.6 (4)C16—C11—C12—Br12178.09 (17)
C4—N1—C3—C2177.4 (4)C4—C11—C12—Br120.7 (3)
C3'—N1—C3—C2172.0 (15)C11—C12—C13—C140.3 (3)
S1—C2—C3—O2177.8 (3)Br12—C12—C13—C14178.87 (17)
S1—C2—C3—N12.2 (5)C42—O41—C14—C130.6 (3)
C3—N1—C1'—O1'178.4 (15)C42—O41—C14—C15179.4 (2)
C1—N1—C1'—O1'5 (2)C12—C13—C14—O41179.7 (2)
C4—N1—C1'—O1'2 (2)C12—C13—C14—C150.3 (3)
C3'—N1—C1'—O1'176.6 (14)C52—O51—C15—C167.1 (4)
C3—N1—C1'—C2'2.0 (13)C52—O51—C15—C14172.9 (2)
C1—N1—C1'—C2'178 (4)O41—C14—C15—O510.5 (3)
C4—N1—C1'—C2'177.9 (6)C13—C14—C15—O51179.5 (2)
C3'—N1—C1'—C2'7.0 (17)O41—C14—C15—C16179.5 (2)
N1—C1'—C2'—S1'5.3 (16)C13—C14—C15—C160.5 (3)
O1'—C1'—C2'—S1'178.8 (17)O51—C15—C16—C11178.8 (2)
C3'—S1'—C2'—C1'1.9 (12)C14—C15—C16—C111.3 (4)
C1'—N1—C3'—O2'170.1 (17)C12—C11—C16—C151.2 (3)
C3—N1—C3'—O2'177 (3)C4—C11—C16—C15178.7 (2)
 

Follow Acta Cryst. E
Sign up for e-alerts
Follow Acta Cryst. on Twitter
Follow us on facebook
Sign up for RSS feeds