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The title compound, C15H12BrNO5S, is a chalcone derivative with potential nonlinear optical (NLO) properties. The mol­ecule is essentially planar and does not show any unusual geometric parameters. The mol­ecular structure and the crystal packing are characterized by C—H...Br and C—H...O contacts.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536806032284/lh2160sup1.cif
Contains datablocks I, global

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S1600536806032284/lh2160Isup2.hkl
Contains datablock I

CCDC reference: 621414

Key indicators

  • Single-crystal X-ray study
  • T = 173 K
  • Mean [sigma](C-C) = 0.005 Å
  • R factor = 0.049
  • wR factor = 0.127
  • Data-to-parameter ratio = 13.8

checkCIF/PLATON results

No syntax errors found



Alert level C PLAT062_ALERT_4_C Rescale T(min) & T(max) by ..................... 0.94 PLAT431_ALERT_2_C Short Inter HL..A Contact Br1 .. O11 .. 3.26 Ang. PLAT431_ALERT_2_C Short Inter HL..A Contact Br1 .. Br1 .. 3.59 Ang.
Alert level G ABSTM02_ALERT_3_G When printed, the submitted absorption T values will be replaced by the scaled T values. Since the ratio of scaled T's is identical to the ratio of reported T values, the scaling does not imply a change to the absorption corrections used in the study. Ratio of Tmax expected/reported 0.935 Tmax scaled 0.540 Tmin scaled 0.298
0 ALERT level A = In general: serious problem 0 ALERT level B = Potentially serious problem 3 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 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 1 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: PLATON (Spek, 2003); software used to prepare material for publication: SHELXL97.

(2E)-1-(3-Bromo-2-thienyl)-3-(4,5-dimethoxy-2-nitrophenyl)prop-2-en-1-one top
Crystal data top
C15H12BrNO5SF(000) = 800
Mr = 398.23Dx = 1.700 Mg m3
Monoclinic, P21/cMo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybcCell parameters from 7122 reflections
a = 8.9032 (10) Åθ = 3.6–25.4°
b = 9.0892 (7) ŵ = 2.80 mm1
c = 19.307 (2) ÅT = 173 K
β = 95.174 (9)°Plate, brown
V = 1556.0 (3) Å30.46 × 0.43 × 0.22 mm
Z = 4
Data collection top
Stoe IPDS-II two-circle
diffractometer
2911 independent reflections
Radiation source: fine-focus sealed tube2507 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.063
ω scansθmax = 25.7°, θmin = 3.7°
Absorption correction: multi-scan
(MULABS; Spek, 2003; Blessing, 1995)
h = 1010
Tmin = 0.319, Tmax = 0.578k = 1110
8965 measured reflectionsl = 2323
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)] = 0.050H-atom parameters constrained
wR(F2) = 0.127 w = 1/[σ2(Fo2) + (0.0774P)2 + 1.2577P]
where P = (Fo2 + 2Fc2)/3
S = 1.05(Δ/σ)max < 0.001
2911 reflectionsΔρmax = 1.22 e Å3
211 parametersΔρmin = 1.07 e Å3
0 restraintsExtinction correction: SHELXL97, Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4
Primary atom site location: structure-invariant direct methodsExtinction coefficient: 0.0082 (15)
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
Br10.51964 (4)0.13147 (4)0.43194 (2)0.03432 (19)
S10.30044 (11)0.36435 (11)0.24880 (5)0.0318 (3)
C10.4150 (4)0.3499 (4)0.32687 (18)0.0224 (7)
C20.4174 (4)0.2057 (4)0.34921 (18)0.0241 (7)
C30.3293 (4)0.1091 (4)0.3041 (2)0.0332 (9)
H30.31950.00660.31230.040*
C40.2606 (5)0.1805 (5)0.2477 (2)0.0372 (9)
H40.19780.13340.21200.045*
C50.4806 (4)0.4917 (4)0.35447 (17)0.0220 (7)
O50.4310 (3)0.6075 (3)0.32960 (14)0.0301 (6)
C60.6076 (4)0.4888 (4)0.41068 (17)0.0250 (7)
H60.65350.39780.42440.030*
C70.6568 (4)0.6125 (4)0.44156 (18)0.0228 (7)
H70.61100.70180.42520.027*
C110.7771 (4)0.6220 (4)0.49939 (17)0.0196 (7)
C120.8516 (4)0.7527 (4)0.52028 (16)0.0201 (7)
C130.9546 (4)0.7638 (4)0.57899 (16)0.0202 (7)
H131.00000.85580.59150.024*
C140.9902 (4)0.6400 (4)0.61891 (17)0.0205 (7)
C150.9167 (3)0.5046 (4)0.60014 (17)0.0199 (7)
C160.8125 (4)0.4980 (4)0.54225 (17)0.0208 (7)
H160.76330.40730.53100.025*
N10.8260 (3)0.8884 (3)0.47960 (16)0.0233 (6)
O110.8323 (3)1.0063 (3)0.51144 (15)0.0341 (6)
O120.8030 (3)0.8804 (3)0.41579 (14)0.0330 (6)
O171.0921 (3)0.6364 (3)0.67588 (13)0.0250 (5)
C171.1641 (4)0.7747 (4)0.69620 (19)0.0298 (8)
H17A1.20830.81790.65620.045*
H17B1.24360.75740.73380.045*
H17C1.08900.84250.71230.045*
O180.9567 (3)0.3892 (3)0.64273 (13)0.0256 (5)
C180.8873 (4)0.2496 (4)0.6252 (2)0.0295 (8)
H18A0.77800.25750.62730.044*
H18B0.92790.17480.65830.044*
H18C0.90860.22140.57810.044*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
Br10.0370 (3)0.0353 (3)0.0304 (3)0.00717 (15)0.00160 (16)0.01153 (16)
S10.0353 (5)0.0376 (6)0.0208 (5)0.0041 (4)0.0071 (4)0.0037 (4)
C10.0207 (15)0.0288 (18)0.0175 (16)0.0025 (13)0.0003 (12)0.0022 (13)
C20.0208 (15)0.0311 (19)0.0199 (16)0.0040 (13)0.0006 (13)0.0015 (14)
C30.0322 (19)0.031 (2)0.037 (2)0.0055 (15)0.0055 (17)0.0099 (17)
C40.035 (2)0.044 (2)0.032 (2)0.0074 (17)0.0027 (16)0.0182 (19)
C50.0216 (15)0.0296 (18)0.0149 (15)0.0024 (13)0.0029 (12)0.0052 (14)
O50.0340 (13)0.0268 (13)0.0278 (14)0.0036 (10)0.0070 (11)0.0018 (11)
C60.0267 (16)0.0286 (18)0.0185 (16)0.0014 (13)0.0041 (14)0.0033 (14)
C70.0228 (15)0.0288 (17)0.0162 (16)0.0017 (13)0.0013 (13)0.0012 (13)
C110.0213 (15)0.0246 (17)0.0127 (15)0.0000 (12)0.0004 (12)0.0037 (13)
C120.0241 (15)0.0226 (17)0.0136 (15)0.0021 (13)0.0015 (12)0.0015 (13)
C130.0221 (15)0.0222 (16)0.0158 (15)0.0031 (13)0.0005 (12)0.0031 (13)
C140.0219 (15)0.0266 (17)0.0124 (15)0.0007 (13)0.0015 (12)0.0039 (13)
C150.0220 (15)0.0227 (17)0.0148 (15)0.0023 (13)0.0008 (12)0.0021 (13)
C160.0227 (15)0.0226 (17)0.0166 (15)0.0013 (13)0.0001 (12)0.0047 (13)
N10.0218 (13)0.0226 (15)0.0246 (16)0.0004 (11)0.0021 (12)0.0017 (12)
O110.0406 (15)0.0196 (13)0.0398 (15)0.0005 (11)0.0085 (12)0.0028 (12)
O120.0441 (15)0.0360 (15)0.0177 (13)0.0045 (12)0.0031 (11)0.0059 (11)
O170.0300 (12)0.0265 (13)0.0168 (12)0.0024 (10)0.0072 (10)0.0030 (9)
C170.0323 (18)0.034 (2)0.0214 (18)0.0106 (15)0.0053 (14)0.0043 (15)
O180.0349 (13)0.0196 (12)0.0208 (12)0.0016 (10)0.0049 (10)0.0002 (10)
C180.0357 (18)0.0199 (17)0.033 (2)0.0006 (15)0.0022 (15)0.0000 (15)
Geometric parameters (Å, º) top
Br1—C21.890 (3)C12—N11.469 (4)
S1—C41.708 (5)C13—C141.384 (5)
S1—C11.747 (3)C13—H130.9500
C1—C21.379 (5)C14—O171.361 (4)
C1—C51.494 (5)C14—C151.426 (5)
C2—C31.422 (5)C15—O181.360 (4)
C3—C41.364 (6)C15—C161.388 (5)
C3—H30.9500C16—H160.9500
C4—H40.9500N1—O121.233 (4)
C5—O51.223 (4)N1—O111.234 (4)
C5—C61.495 (5)O17—C171.449 (4)
C6—C71.328 (5)C17—H17A0.9800
C6—H60.9500C17—H17B0.9800
C7—C111.479 (4)C17—H17C0.9800
C7—H70.9500O18—C181.439 (4)
C11—C121.401 (5)C18—H18A0.9800
C11—C161.417 (5)C18—H18B0.9800
C12—C131.396 (4)C18—H18C0.9800
C4—S1—C192.36 (19)C14—C13—H13120.2
C2—C1—C5135.6 (3)C12—C13—H13120.2
C2—C1—S1109.4 (3)O17—C14—C13124.9 (3)
C5—C1—S1115.0 (3)O17—C14—C15116.2 (3)
C1—C2—C3113.8 (3)C13—C14—C15118.9 (3)
C1—C2—Br1126.6 (3)O18—C15—C16125.0 (3)
C3—C2—Br1119.6 (3)O18—C15—C14115.0 (3)
C4—C3—C2112.2 (4)C16—C15—C14120.0 (3)
C4—C3—H3123.9C15—C16—C11122.2 (3)
C2—C3—H3123.9C15—C16—H16118.9
C3—C4—S1112.2 (3)C11—C16—H16118.9
C3—C4—H4123.9O12—N1—O11123.0 (3)
S1—C4—H4123.9O12—N1—C12119.2 (3)
O5—C5—C1119.2 (3)O11—N1—C12117.7 (3)
O5—C5—C6121.5 (3)C14—O17—C17116.3 (3)
C1—C5—C6119.3 (3)O17—C17—H17A109.5
C7—C6—C5120.5 (3)O17—C17—H17B109.5
C7—C6—H6119.7H17A—C17—H17B109.5
C5—C6—H6119.7O17—C17—H17C109.5
C6—C7—C11125.2 (3)H17A—C17—H17C109.5
C6—C7—H7117.4H17B—C17—H17C109.5
C11—C7—H7117.4C15—O18—C18117.0 (3)
C12—C11—C16115.5 (3)O18—C18—H18A109.5
C12—C11—C7124.0 (3)O18—C18—H18B109.5
C16—C11—C7120.1 (3)H18A—C18—H18B109.5
C13—C12—C11123.7 (3)O18—C18—H18C109.5
C13—C12—N1115.6 (3)H18A—C18—H18C109.5
C11—C12—N1120.7 (3)H18B—C18—H18C109.5
C14—C13—C12119.6 (3)
C4—S1—C1—C20.4 (3)C7—C11—C12—N17.4 (5)
C4—S1—C1—C5178.2 (3)C11—C12—C13—C141.6 (5)
C5—C1—C2—C3177.5 (4)N1—C12—C13—C14177.5 (3)
S1—C1—C2—C30.3 (4)C12—C13—C14—O17177.9 (3)
C5—C1—C2—Br11.1 (6)C12—C13—C14—C152.0 (5)
S1—C1—C2—Br1178.21 (19)O17—C14—C15—O181.0 (4)
C1—C2—C3—C40.0 (5)C13—C14—C15—O18179.1 (3)
Br1—C2—C3—C4178.7 (3)O17—C14—C15—C16179.2 (3)
C2—C3—C4—S10.4 (4)C13—C14—C15—C160.7 (5)
C1—S1—C4—C30.5 (3)O18—C15—C16—C11179.2 (3)
C2—C1—C5—O5164.0 (4)C14—C15—C16—C111.1 (5)
S1—C1—C5—O513.1 (4)C12—C11—C16—C151.5 (5)
C2—C1—C5—C617.5 (6)C7—C11—C16—C15175.2 (3)
S1—C1—C5—C6165.5 (3)C13—C12—N1—O12144.7 (3)
O5—C5—C6—C79.0 (5)C11—C12—N1—O1234.4 (5)
C1—C5—C6—C7172.4 (3)C13—C12—N1—O1133.6 (4)
C5—C6—C7—C11177.5 (3)C11—C12—N1—O11147.3 (3)
C6—C7—C11—C12164.3 (4)C13—C14—O17—C171.7 (5)
C6—C7—C11—C1622.5 (5)C15—C14—O17—C17178.4 (3)
C16—C11—C12—C130.1 (5)C16—C15—O18—C181.2 (5)
C7—C11—C12—C13173.6 (3)C14—C15—O18—C18179.0 (3)
C16—C11—C12—N1179.2 (3)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
C6—H6···Br10.952.713.375 (4)128
C7—H7···O50.952.492.816 (4)100
C7—H7···O120.952.382.826 (4)109
C4—H4···O18i0.952.433.292 (5)150
C18—H18A···O5ii0.982.443.305 (5)147
C18—H18C···O11iii0.982.413.125 (4)130
Symmetry codes: (i) x1, y+1/2, z1/2; (ii) x+1, y+1, z+1; (iii) x, y1, z.
 

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