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The title mol­ecule, C18H17ClO4, deviates slightly from planarity with a dihedral angle of 27.18 (11)° between the rings. The crystal structure is stabilized by inter­molecular C—H...O and C—H...Br inter­actions.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536806050641/sj2182sup1.cif
Contains datablocks global, I

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S1600536806050641/sj2182Isup2.hkl
Contains datablock I

CCDC reference: 634004

Key indicators

  • Single-crystal X-ray study
  • T = 100 K
  • Mean [sigma](C-C) = 0.003 Å
  • R factor = 0.035
  • wR factor = 0.098
  • Data-to-parameter ratio = 39.4

checkCIF/PLATON results

No syntax errors found



Alert level C PLAT062_ALERT_4_C Rescale T(min) & T(max) by ..................... 0.75 PLAT063_ALERT_3_C Crystal Probably too Large for Beam Size ....... 0.63 mm PLAT480_ALERT_4_C Long H...A H-Bond Reported H1A .. BR1 .. 2.97 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 0.755 Tmax scaled 0.266 Tmin scaled 0.168 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 37.50 From the CIF: _reflns_number_total 6420 Count of symmetry unique reflns 3716 Completeness (_total/calc) 172.77% TEST3: Check Friedels for noncentro structure Estimate of Friedel pairs measured 2704 Fraction of Friedel pairs measured 0.728 Are heavy atom types Z>Si present yes
0 ALERT level A = In general: serious problem 0 ALERT level B = Potentially serious problem 3 ALERT level C = Check and explain 2 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 2 ALERT type 3 Indicator that the structure quality may be low 3 ALERT type 4 Improvement, methodology, query or suggestion 0 ALERT type 5 Informative message, check

Computing details top

Data collection: APEX2 (Bruker, 2005); cell refinement: APEX2; data reduction: SAINT (Bruker, 2005); program(s) used to solve structure: SHELXTL (Sheldrick, 1998); program(s) used to refine structure: SHELXTL; molecular graphics: SHELXTL; software used to prepare material for publication: SHELXTL, PARST (Nardelli, 1995) and PLATON (Spek, 2003).

3-(5-Bromo-2-thienyl)-1-(4-methoxyphenyl)prop-2-en-1-one top
Crystal data top
C14H11BrO2SF(000) = 648
Mr = 323.20Dx = 1.692 Mg m3
Orthorhombic, Pna21Mo Kα radiation, λ = 0.71073 Å
Hall symbol: P 2c -2nCell parameters from 5719 reflections
a = 10.1774 (2) Åθ = 1.3–37.5°
b = 31.8924 (6) ŵ = 3.40 mm1
c = 3.9078 (1) ÅT = 100 K
V = 1268.40 (5) Å3Block, yellow
Z = 40.63 × 0.47 × 0.39 mm
Data collection top
Bruker SMART APEX2 CCD area-detector
diffractometer
6420 independent reflections
Radiation source: fine-focus sealed tube5576 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.035
Detector resolution: 8.33 pixels mm-1θmax = 37.5°, θmin = 1.3°
ω scansh = 1717
Absorption correction: multi-scan
(SADABS; Bruker, 2005)
k = 5454
Tmin = 0.222, Tmax = 0.353l = 66
27460 measured reflections
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)] = 0.035H-atom parameters constrained
wR(F2) = 0.099 w = 1/[σ2(Fo2) + (0.0488P)2 + 0.3039P]
where P = (Fo2 + 2Fc2)/3
S = 1.11(Δ/σ)max < 0.001
6420 reflectionsΔρmax = 0.81 e Å3
163 parametersΔρmin = 0.70 e Å3
1 restraintAbsolute structure: Flack (1983), 2706 Friedel pairs
Primary atom site location: structure-invariant direct methodsAbsolute structure parameter: 0.092 (7)
Special details top

Experimental. The data was collected with the Oxford Cyrosystem Cobra low-temperature attachment.

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
Br10.489217 (19)0.207371 (5)1.25250 (10)0.02237 (5)
S10.36412 (5)0.287385 (13)0.94118 (15)0.01710 (8)
O10.27161 (14)0.44656 (5)0.5147 (5)0.0235 (3)
O20.34753 (14)0.42747 (4)0.4202 (5)0.0213 (3)
C10.02792 (18)0.38669 (5)0.6359 (6)0.0166 (3)
H1A0.00630.36330.74600.020*
C20.16200 (19)0.39057 (6)0.5968 (6)0.0180 (3)
H2A0.21760.36960.67660.022*
C30.21429 (17)0.42616 (5)0.4364 (6)0.0163 (3)
C40.13115 (17)0.45723 (5)0.3087 (5)0.0166 (3)
H4A0.16550.48080.20020.020*
C50.00350 (17)0.45251 (6)0.3462 (6)0.0165 (3)
H5A0.05910.47300.25920.020*
C60.05774 (18)0.41777 (5)0.5110 (5)0.0150 (3)
C70.20228 (18)0.41558 (6)0.5664 (6)0.0171 (3)
C80.25866 (18)0.37555 (5)0.6879 (5)0.0184 (4)
H8A0.20870.35120.67260.022*
C90.38022 (18)0.37347 (5)0.8197 (5)0.0179 (3)
H9A0.42910.39810.82690.021*
C100.44062 (17)0.33598 (5)0.9508 (6)0.0163 (3)
C110.56244 (19)0.33299 (6)1.1039 (6)0.0192 (3)
H11A0.61830.35581.13170.023*
C120.59456 (19)0.29186 (6)1.2149 (7)0.0199 (4)
H12A0.67240.28461.32460.024*
C130.49588 (17)0.26442 (6)1.1392 (6)0.0176 (3)
C140.40667 (17)0.46361 (6)0.2643 (8)0.0233 (3)
H14A0.50050.46070.26720.035*
H14B0.37690.46600.03210.035*
H14C0.38210.48830.38950.035*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
Br10.02979 (10)0.01561 (7)0.02171 (9)0.00435 (6)0.00052 (11)0.00191 (9)
S10.01695 (17)0.01388 (14)0.0205 (2)0.00004 (13)0.00072 (16)0.00056 (16)
O10.0179 (6)0.0153 (5)0.0375 (10)0.0020 (4)0.0003 (6)0.0032 (6)
O20.0166 (5)0.0166 (5)0.0308 (8)0.0003 (4)0.0011 (6)0.0017 (6)
C10.0201 (7)0.0112 (6)0.0184 (8)0.0001 (5)0.0005 (6)0.0005 (6)
C20.0187 (7)0.0138 (6)0.0215 (9)0.0023 (5)0.0020 (7)0.0019 (6)
C30.0162 (7)0.0144 (6)0.0183 (8)0.0003 (5)0.0006 (6)0.0004 (6)
C40.0190 (7)0.0133 (6)0.0176 (9)0.0002 (5)0.0008 (6)0.0001 (6)
C50.0176 (7)0.0134 (6)0.0185 (8)0.0004 (5)0.0004 (6)0.0003 (6)
C60.0162 (7)0.0124 (6)0.0165 (8)0.0005 (5)0.0004 (6)0.0002 (5)
C70.0177 (7)0.0141 (7)0.0196 (8)0.0006 (5)0.0009 (6)0.0005 (6)
C80.0194 (7)0.0125 (6)0.0234 (11)0.0010 (5)0.0018 (6)0.0008 (6)
C90.0195 (7)0.0133 (6)0.0207 (9)0.0001 (5)0.0000 (6)0.0008 (6)
C100.0166 (7)0.0164 (6)0.0160 (8)0.0000 (5)0.0003 (6)0.0006 (6)
C110.0168 (7)0.0193 (7)0.0215 (9)0.0004 (6)0.0011 (7)0.0003 (7)
C120.0183 (7)0.0207 (7)0.0207 (11)0.0028 (5)0.0011 (7)0.0002 (7)
C130.0178 (7)0.0161 (7)0.0190 (8)0.0035 (5)0.0009 (6)0.0011 (6)
C140.0191 (7)0.0231 (7)0.0277 (10)0.0042 (5)0.0012 (10)0.0015 (10)
Geometric parameters (Å, º) top
Br1—C131.874 (2)C5—H5A0.9300
S1—C131.713 (2)C6—C71.489 (3)
S1—C101.7349 (18)C7—C81.478 (3)
O1—C71.231 (2)C8—C91.342 (3)
O2—C31.358 (2)C8—H8A0.9300
O2—C141.436 (3)C9—C101.438 (3)
C1—C21.379 (3)C9—H9A0.9300
C1—C61.407 (3)C10—C111.380 (3)
C1—H1A0.9300C11—C121.420 (3)
C2—C31.402 (3)C11—H11A0.9300
C2—H2A0.9300C12—C131.364 (3)
C3—C41.395 (3)C12—H12A0.9300
C4—C51.386 (2)C14—H14A0.9600
C4—H4A0.9300C14—H14B0.9600
C5—C61.395 (3)C14—H14C0.9600
C13—S1—C1091.19 (9)C9—C8—H8A119.2
C3—O2—C14117.59 (15)C7—C8—H8A119.2
C2—C1—C6120.77 (17)C8—C9—C10124.89 (17)
C2—C1—H1A119.6C8—C9—H9A117.6
C6—C1—H1A119.6C10—C9—H9A117.6
C1—C2—C3119.86 (17)C11—C10—C9126.57 (17)
C1—C2—H2A120.1C11—C10—S1110.53 (14)
C3—C2—H2A120.1C9—C10—S1122.89 (14)
O2—C3—C4124.53 (17)C10—C11—C12113.79 (17)
O2—C3—C2115.15 (16)C10—C11—H11A123.1
C4—C3—C2120.32 (16)C12—C11—H11A123.1
C5—C4—C3118.98 (17)C13—C12—C11110.90 (18)
C5—C4—H4A120.5C13—C12—H12A124.6
C3—C4—H4A120.5C11—C12—H12A124.6
C4—C5—C6121.74 (17)C12—C13—S1113.59 (15)
C4—C5—H5A119.1C12—C13—Br1126.73 (15)
C6—C5—H5A119.1S1—C13—Br1119.58 (11)
C5—C6—C1118.31 (17)O2—C14—H14A109.5
C5—C6—C7119.70 (16)O2—C14—H14B109.5
C1—C6—C7121.91 (16)H14A—C14—H14B109.5
O1—C7—C8121.56 (17)O2—C14—H14C109.5
O1—C7—C6120.33 (16)H14A—C14—H14C109.5
C8—C7—C6118.11 (15)H14B—C14—H14C109.5
C9—C8—C7121.62 (16)
C6—C1—C2—C31.1 (3)C1—C6—C7—C813.5 (3)
C14—O2—C3—C40.8 (3)O1—C7—C8—C915.2 (3)
C14—O2—C3—C2178.9 (2)C6—C7—C8—C9164.09 (19)
C1—C2—C3—O2178.1 (2)C7—C8—C9—C10178.4 (2)
C1—C2—C3—C41.5 (3)C8—C9—C10—C11176.5 (2)
O2—C3—C4—C5178.9 (2)C8—C9—C10—S12.3 (3)
C2—C3—C4—C50.6 (3)C13—S1—C10—C110.16 (18)
C3—C4—C5—C60.7 (3)C13—S1—C10—C9179.08 (19)
C4—C5—C6—C11.0 (3)C9—C10—C11—C12178.6 (2)
C4—C5—C6—C7175.7 (2)S1—C10—C11—C120.2 (3)
C2—C1—C6—C50.1 (3)C10—C11—C12—C130.6 (3)
C2—C1—C6—C7176.6 (2)C11—C12—C13—S10.8 (3)
C5—C6—C7—O110.8 (3)C11—C12—C13—Br1176.94 (17)
C1—C6—C7—O1165.9 (2)C10—S1—C13—C120.5 (2)
C5—C6—C7—C8169.89 (19)C10—S1—C13—Br1177.02 (14)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
C8—H8A···S10.932.783.168 (2)106
C11—H11A···O2i0.932.573.383 (2)146
C14—H14A···O1ii0.962.553.460 (2)158
C1—H1A···Br1iii0.932.973.358 (2)107
Symmetry codes: (i) x+1, y, z+1; (ii) x1, y, z; (iii) x1/2, y+1/2, z1.
 

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