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In the title compound, C19H13Br2NO4S2, the two bromo­thienyl rings have different orientations with respect to the carbonyl groups. The nitro group is almost coplanar with the benzene ring to which it is attached.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536806036993/sg2053sup1.cif
Contains datablocks I, global

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S1600536806036993/sg2053Isup2.hkl
Contains datablock I

CCDC reference: 624973

Key indicators

  • Single-crystal X-ray study
  • T = 173 K
  • Mean [sigma](C-C) = 0.005 Å
  • R factor = 0.042
  • wR factor = 0.112
  • Data-to-parameter ratio = 17.4

checkCIF/PLATON results

No syntax errors found



Alert level C PLAT062_ALERT_4_C Rescale T(min) & T(max) by ..................... 0.95
Alert level G REFLT03_ALERT_4_G Please check that the estimate of the number of Friedel pairs is correct. If it is not, please give the correct count in the _publ_section_exptl_refinement section of the submitted CIF. From the CIF: _diffrn_reflns_theta_max 27.60 From the CIF: _reflns_number_total 4431 Count of symmetry unique reflns 2368 Completeness (_total/calc) 187.12% TEST3: Check Friedels for noncentro structure Estimate of Friedel pairs measured 2063 Fraction of Friedel pairs measured 0.871 Are heavy atom types Z>Si present yes
0 ALERT level A = In general: serious problem 0 ALERT level B = Potentially serious problem 1 ALERT level C = Check and explain 1 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 0 ALERT type 3 Indicator that the structure quality may be low 2 ALERT type 4 Improvement, methodology, query or suggestion 0 ALERT type 5 Informative message, check

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, 1997); 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).

1,5-Bis(3-bromothien-2-yl)-3-(3-nitrophenyl)pentane-1,5-dione top
Crystal data top
C19H13Br2NO4S2F(000) = 1072
Mr = 543.24Dx = 1.775 Mg m3
Monoclinic, CcMo Kα radiation, λ = 0.71073 Å
Hall symbol: C -2ycCell parameters from 12507 reflections
a = 17.5329 (13) Åθ = 2.6–27.8°
b = 15.6345 (9) ŵ = 4.22 mm1
c = 7.4723 (6) ÅT = 173 K
β = 96.932 (6)°Rod, colourless
V = 2033.3 (3) Å30.26 × 0.13 × 0.12 mm
Z = 4
Data collection top
Stoe IPDS-II two-circle
diffractometer
4431 independent reflections
Radiation source: fine-focus sealed tube4195 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.058
ω scansθmax = 27.6°, θmin = 2.6°
Absorption correction: multi-scan
(MULABS; Spek, 2003; Blessing, 1995)
h = 2222
Tmin = 0.407, Tmax = 0.632k = 2020
13028 measured reflectionsl = 99
Refinement top
Refinement on F2Hydrogen site location: inferred from neighbouring sites
Least-squares matrix: fullH-atom parameters constrained
R[F2 > 2σ(F2)] = 0.042 w = 1/[σ2(Fo2) + (0.0814P)2 + 0.7776P]
where P = (Fo2 + 2Fc2)/3
wR(F2) = 0.112(Δ/σ)max < 0.001
S = 1.04Δρmax = 0.61 e Å3
4431 reflectionsΔρmin = 0.69 e Å3
254 parametersExtinction correction: SHELXL97, Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4
2 restraintsExtinction coefficient: 0.0066 (6)
Primary atom site location: structure-invariant direct methodsAbsolute structure: Flack (1983)
Secondary atom site location: difference Fourier mapAbsolute structure parameter: 0.002 (8)
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
N10.5105 (2)0.1428 (2)0.2398 (5)0.0322 (6)
O10.4939 (2)0.19548 (19)0.1192 (4)0.0444 (7)
O20.5124 (2)0.06581 (19)0.2108 (4)0.0481 (7)
C10.54947 (19)0.2923 (2)0.6297 (4)0.0257 (6)
C20.53247 (19)0.2620 (2)0.4533 (4)0.0247 (6)
H20.52310.30080.35530.030*
C30.5295 (2)0.1746 (2)0.4239 (4)0.0257 (6)
C40.5426 (3)0.1143 (2)0.5616 (6)0.0324 (8)
H40.53950.05470.53720.039*
C50.5604 (3)0.1449 (3)0.7356 (6)0.0398 (9)
H50.57030.10580.83290.048*
C60.5639 (2)0.2325 (2)0.7690 (4)0.0328 (7)
H60.57640.25210.88930.039*
C70.5521 (2)0.3870 (2)0.6671 (5)0.0256 (7)
H70.53640.41780.55110.031*
S110.39175 (7)0.38417 (6)1.09916 (13)0.0360 (2)
C110.3583 (2)0.3862 (2)0.8709 (5)0.0309 (7)
C120.2795 (3)0.3793 (3)0.8499 (6)0.0386 (9)
Br120.21502 (3)0.38086 (4)0.62852 (5)0.05515 (18)
C130.2473 (3)0.3724 (4)1.0146 (7)0.0530 (12)
H130.19380.36741.02260.064*
C140.3020 (3)0.3738 (4)1.1592 (7)0.0500 (12)
H140.29130.36941.28050.060*
C150.4126 (2)0.3923 (2)0.7340 (5)0.0289 (7)
O150.3902 (2)0.3829 (2)0.5729 (4)0.0429 (7)
C160.4954 (2)0.4117 (3)0.8017 (5)0.0301 (7)
H16A0.50970.38050.91610.036*
H16B0.50050.47370.82800.036*
S210.73682 (8)0.65191 (7)0.80025 (15)0.0438 (3)
C210.7274 (2)0.5414 (2)0.7933 (4)0.0302 (7)
C220.7989 (2)0.5044 (3)0.8373 (4)0.0347 (8)
Br220.82057 (2)0.38621 (3)0.85481 (4)0.04393 (14)
C230.8600 (3)0.5637 (3)0.8733 (6)0.0469 (10)
H230.91240.54820.90340.056*
C240.8339 (3)0.6453 (3)0.8592 (7)0.0541 (12)
H240.86620.69400.88000.065*
C250.6485 (2)0.5095 (2)0.7414 (4)0.0280 (6)
O250.59697 (18)0.56033 (18)0.7008 (4)0.0400 (6)
C260.63504 (19)0.4136 (2)0.7371 (4)0.0252 (6)
H26A0.64810.39070.86050.030*
H26B0.67040.38700.65960.030*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
N10.0305 (17)0.0304 (13)0.0369 (14)0.0035 (13)0.0086 (12)0.0088 (13)
O10.063 (2)0.0420 (15)0.0274 (12)0.0094 (14)0.0020 (13)0.0064 (11)
O20.0580 (19)0.0304 (13)0.0554 (18)0.0001 (14)0.0047 (16)0.0171 (12)
C10.0234 (15)0.0291 (15)0.0240 (14)0.0066 (12)0.0008 (12)0.0012 (12)
C20.0231 (15)0.0264 (14)0.0243 (13)0.0022 (12)0.0017 (11)0.0003 (11)
C30.0243 (15)0.0252 (14)0.0273 (15)0.0039 (12)0.0022 (12)0.0024 (11)
C40.031 (2)0.0265 (15)0.0394 (19)0.0049 (12)0.0043 (16)0.0049 (13)
C50.045 (2)0.0355 (19)0.0377 (19)0.0088 (17)0.0009 (17)0.0110 (15)
C60.0369 (19)0.0362 (17)0.0247 (14)0.0104 (15)0.0010 (13)0.0022 (13)
C70.0246 (18)0.0272 (15)0.0249 (14)0.0023 (12)0.0025 (13)0.0041 (11)
S110.0290 (5)0.0484 (5)0.0298 (4)0.0035 (4)0.0010 (4)0.0016 (3)
C110.0272 (19)0.0363 (18)0.0280 (16)0.0018 (13)0.0017 (14)0.0046 (12)
C120.027 (2)0.051 (2)0.037 (2)0.0013 (15)0.0015 (17)0.0034 (16)
Br120.0274 (2)0.0933 (4)0.0419 (2)0.0036 (2)0.00693 (18)0.0033 (2)
C130.030 (2)0.090 (4)0.040 (2)0.002 (2)0.0080 (19)0.000 (2)
C140.037 (3)0.077 (3)0.039 (2)0.007 (2)0.014 (2)0.005 (2)
C150.0247 (18)0.0307 (17)0.0304 (16)0.0003 (12)0.0009 (14)0.0028 (12)
O150.0303 (16)0.067 (2)0.0298 (13)0.0041 (13)0.0044 (12)0.0081 (12)
C160.0222 (16)0.0393 (17)0.0287 (15)0.0066 (15)0.0026 (13)0.0071 (14)
S210.0497 (6)0.0352 (5)0.0464 (5)0.0161 (5)0.0051 (4)0.0060 (4)
C210.0339 (17)0.0340 (16)0.0230 (13)0.0077 (14)0.0043 (12)0.0045 (12)
C220.0311 (18)0.049 (2)0.0241 (16)0.0089 (15)0.0039 (14)0.0004 (13)
Br220.0295 (2)0.0495 (2)0.0522 (2)0.00010 (17)0.00246 (19)0.00521 (19)
C230.035 (2)0.064 (3)0.041 (2)0.020 (2)0.0007 (17)0.0012 (19)
C240.051 (3)0.058 (3)0.052 (2)0.030 (2)0.001 (2)0.005 (2)
C250.0280 (17)0.0335 (16)0.0218 (13)0.0044 (13)0.0001 (12)0.0022 (11)
O250.0364 (15)0.0324 (12)0.0496 (14)0.0012 (11)0.0010 (12)0.0039 (11)
C260.0211 (15)0.0266 (14)0.0276 (14)0.0044 (13)0.0020 (12)0.0051 (12)
Geometric parameters (Å, º) top
N1—O21.225 (4)C12—Br121.888 (4)
N1—O11.229 (5)C13—C141.356 (8)
N1—C31.463 (4)C13—H130.9500
C1—C21.399 (4)C14—H140.9500
C1—C61.400 (5)C15—O151.229 (5)
C1—C71.506 (4)C15—C161.509 (5)
C2—C31.384 (4)C16—H16A0.9900
C2—H20.9500C16—H16B0.9900
C3—C41.393 (5)S21—C241.709 (6)
C4—C51.385 (6)S21—C211.736 (4)
C4—H40.9500C21—C221.385 (6)
C5—C61.391 (5)C21—C251.477 (5)
C5—H50.9500C22—C231.417 (6)
C6—H60.9500C22—Br221.888 (4)
C7—C261.543 (5)C23—C241.357 (8)
C7—C161.546 (5)C23—H230.9500
C7—H71.0000C24—H240.9500
S11—C141.695 (5)C25—O251.215 (5)
S11—C111.736 (4)C25—C261.517 (5)
C11—C121.377 (6)C26—H26A0.9900
C11—C151.481 (5)C26—H26B0.9900
C12—C131.418 (6)
O2—N1—O1122.5 (3)C12—C13—H13124.0
O2—N1—C3119.5 (3)C13—C14—S11112.4 (4)
O1—N1—C3118.0 (3)C13—C14—H14123.8
C2—C1—C6118.2 (3)S11—C14—H14123.8
C2—C1—C7120.4 (3)O15—C15—C11120.8 (4)
C6—C1—C7121.4 (3)O15—C15—C16122.2 (4)
C3—C2—C1119.0 (3)C11—C15—C16117.0 (3)
C3—C2—H2120.5C15—C16—C7113.5 (3)
C1—C2—H2120.5C15—C16—H16A108.9
C2—C3—C4123.4 (3)C7—C16—H16A108.9
C2—C3—N1118.9 (3)C15—C16—H16B108.9
C4—C3—N1117.7 (3)C7—C16—H16B108.9
C5—C4—C3117.3 (3)H16A—C16—H16B107.7
C5—C4—H4121.4C24—S21—C2192.1 (2)
C3—C4—H4121.4C22—C21—C25135.5 (3)
C4—C5—C6120.6 (3)C22—C21—S21109.2 (3)
C4—C5—H5119.7C25—C21—S21115.3 (3)
C6—C5—H5119.7C21—C22—C23114.5 (4)
C5—C6—C1121.6 (3)C21—C22—Br22126.5 (3)
C5—C6—H6119.2C23—C22—Br22119.1 (3)
C1—C6—H6119.2C24—C23—C22111.1 (4)
C1—C7—C26109.5 (3)C24—C23—H23124.4
C1—C7—C16111.0 (3)C22—C23—H23124.4
C26—C7—C16111.5 (3)C23—C24—S21113.1 (3)
C1—C7—H7108.2C23—C24—H24123.4
C26—C7—H7108.2S21—C24—H24123.4
C16—C7—H7108.2O25—C25—C21119.3 (3)
C14—S11—C1192.8 (2)O25—C25—C26122.1 (3)
C12—C11—C15130.3 (3)C21—C25—C26118.6 (3)
C12—C11—S11109.0 (3)C25—C26—C7114.3 (3)
C15—C11—S11120.7 (3)C25—C26—H26A108.7
C11—C12—C13114.0 (4)C7—C26—H26A108.7
C11—C12—Br12125.8 (3)C25—C26—H26B108.7
C13—C12—Br12120.2 (3)C7—C26—H26B108.7
C14—C13—C12111.9 (4)H26A—C26—H26B107.6
C14—C13—H13124.0
C6—C1—C2—C30.9 (5)C11—S11—C14—C130.5 (4)
C7—C1—C2—C3179.1 (3)C12—C11—C15—O157.5 (6)
C1—C2—C3—C40.0 (5)S11—C11—C15—O15170.7 (3)
C1—C2—C3—N1179.0 (3)C12—C11—C15—C16171.6 (4)
O2—N1—C3—C2175.5 (4)S11—C11—C15—C1610.1 (4)
O1—N1—C3—C23.8 (5)O15—C15—C16—C720.7 (5)
O2—N1—C3—C45.4 (5)C11—C15—C16—C7160.2 (3)
O1—N1—C3—C4175.2 (4)C1—C7—C16—C1561.4 (4)
C2—C3—C4—C50.9 (6)C26—C7—C16—C15176.2 (3)
N1—C3—C4—C5179.9 (4)C24—S21—C21—C220.3 (3)
C3—C4—C5—C60.7 (6)C24—S21—C21—C25178.9 (3)
C4—C5—C6—C10.2 (7)C25—C21—C22—C23178.1 (4)
C2—C1—C6—C51.0 (6)S21—C21—C22—C230.8 (4)
C7—C1—C6—C5179.0 (4)C25—C21—C22—Br222.5 (6)
C2—C1—C7—C26113.7 (3)S21—C21—C22—Br22178.52 (19)
C6—C1—C7—C2666.2 (4)C21—C22—C23—C241.0 (5)
C2—C1—C7—C16122.8 (3)Br22—C22—C23—C24178.3 (3)
C6—C1—C7—C1657.3 (4)C22—C23—C24—S210.8 (5)
C14—S11—C11—C120.4 (3)C21—S21—C24—C230.3 (4)
C14—S11—C11—C15178.2 (3)C22—C21—C25—O25176.0 (4)
C15—C11—C12—C13178.2 (4)S21—C21—C25—O252.9 (4)
S11—C11—C12—C130.2 (5)C22—C21—C25—C262.8 (5)
C15—C11—C12—Br123.1 (7)S21—C21—C25—C26178.3 (2)
S11—C11—C12—Br12178.5 (2)O25—C25—C26—C73.3 (5)
C11—C12—C13—C140.2 (7)C21—C25—C26—C7175.5 (3)
Br12—C12—C13—C14179.0 (4)C1—C7—C26—C25167.5 (3)
C12—C13—C14—S110.5 (6)C16—C7—C26—C2569.2 (4)
 

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