(2E)-1-(3-Bromo­phen­yl)-3-(2-thien­yl)prop-2-en-1-one

The thio­phene ring of the title compound, C₁₃H₉BrOS, is disordered. The disorder corresponds to an approximate 180° rotation of the thio­phene ring with respect to the C—C bond linking it to the rest of the mol­ecule. The crystal packing is stabilized by inter­molecular C—H...Br and C—H...π inter­actions, together with short S...Br contacts.

Key indicators

• Single-crystal X-ray study
• T = 100 K
• Mean [sigma](C-C) = 0.002 Å
• Disorder in main residue
• R factor = 0.023
• wR factor = 0.070
• Data-to-parameter ratio = 24.1

checkCIF/PLATON results

No syntax errors found



Alert level C
ABSTM02_ALERT_3_C  The ratio of expected to reported Tmax/Tmin(RR) is > 1.10
            Tmin and Tmax reported:      0.296     0.702
            Tmin and Tmax expected:      0.224     0.683
            RR =      1.283
            Please check that your absorption correction is appropriate.
PLAT060_ALERT_3_C Ratio Tmax/Tmin (Exp-to-Rep) (too) Large .......       1.25
PLAT062_ALERT_4_C Rescale T(min) & T(max) by .....................       0.97
PLAT154_ALERT_1_C The su's on the Cell Angles are Equal (x 10000)         100 Deg.
PLAT180_ALERT_3_C Check Cell Rounding: # of Values Ending with 0 =          4
PLAT301_ALERT_3_C Main Residue  Disorder .........................      20.00 Perc.
PLAT431_ALERT_2_C Short Inter HL..A Contact  Br1    ..  S1X     ..       3.59 Ang.

   0 ALERT level A = In general: serious problem
   0 ALERT level B = Potentially serious problem
   7 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
   1 ALERT type 2 Indicator that the structure model may be wrong or deficient
   4 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


checkCIF publication errors

Alert level A
PUBL024_ALERT_1_A The number of authors is greater than 5.
              Please specify the role of each of the co-authors
              for your paper.

Author Response: H.K. Fun and I.A. Razak are supervisors of Shea-Lin Ng whereas S. M. Dharmaprakash is supervisor of H. B. Ramesh Babu and P. S. Patil in this collaborative pulication. Mangalore University is involved in the extraction and synthesis of the title compound and USM is involved in the structure determination. All parties are involved in writing up the manuscript.

   1 ALERT level A = Data missing that is essential or data in wrong format
   0 ALERT level G = General alerts. Data that may be required is missing

---

Computing details

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).

(2E)-1-(3-bromophenyl)-3-(2-thienyl)prop-2-en-1-one

Crystal data

C13H9BrOS	Z = 2
Mr = 293.17	F(000) = 292
Triclinic, P1	Dx = 1.731 Mg m^−3
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 5.8468 (1) Å	Cell parameters from 9217 reflections
b = 7.4089 (2) Å	θ = 2.8–32.5°
c = 13.1979 (3) Å	µ = 3.81 mm^−1
α = 100.215 (1)°	T = 100 K
β = 91.086 (1)°	Block, yellow
γ = 90.174 (1)°	0.46 × 0.34 × 0.10 mm
V = 562.54 (2) Å^3

Data collection

Bruker SMART APEX2 CCD area-detector diffractometer	4018 independent reflections
Radiation source: fine-focus sealed tube	3615 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.025
Detector resolution: 8.33 pixels mm^-1	θmax = 32.5°, θmin = 2.8°
ω scans	h = −8→8
Absorption correction: multi-scan (SADABS; Bruker, 2005)	k = −11→11
Tmin = 0.296, Tmax = 0.702	l = −19→19
17165 measured reflections

Refinement

Refinement on F^2	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F^2 > 2σ(F^2)] = 0.023	Hydrogen site location: inferred from neighbouring sites
wR(F^2) = 0.070	H-atom parameters constrained
S = 1.13	w = 1/[σ^2(Fo^2) + (0.0319P)^2 + 0.3942P] where P = (Fo^2 + 2Fc^2)/3
4018 reflections	(Δ/σ)max < 0.001
167 parameters	Δρmax = 0.72 e Å^−3
107 restraints	Δρmin = −0.39 e Å^−3

Special details

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 (Ų)

	x	y	z	Uiso*/Ueq	Occ. (<1)
Br1	1.17143 (3)	0.72219 (2)	0.451605 (12)	0.01934 (5)
O1	1.1990 (2)	0.71774 (18)	0.03823 (9)	0.0203 (2)
C1	0.6886 (3)	0.6111 (2)	0.16180 (13)	0.0168 (3)
H1A	0.5901	0.5912	0.1047	0.020*
C2	0.6196 (3)	0.5659 (2)	0.25453 (13)	0.0178 (3)
H2A	0.4764	0.5130	0.2586	0.021*
C3	0.7627 (3)	0.5990 (2)	0.34081 (13)	0.0177 (3)
H3A	0.7164	0.5698	0.4030	0.021*
C4	0.9767 (3)	0.6768 (2)	0.33263 (12)	0.0155 (3)
C5	1.0520 (3)	0.7199 (2)	0.24070 (12)	0.0152 (3)
H5A	1.1968	0.7701	0.2366	0.018*
C6	0.9056 (3)	0.6862 (2)	0.15436 (12)	0.0147 (3)
C7	0.9931 (3)	0.7240 (2)	0.05417 (12)	0.0152 (3)
C8	0.8252 (3)	0.7678 (2)	−0.02296 (12)	0.0166 (3)
H8A	0.6739	0.7920	−0.0049	0.020*
C9	0.8921 (3)	0.7726 (2)	−0.11926 (12)	0.0161 (3)
H9A	1.0432	0.7415	−0.1344	0.019*
C10	0.7520 (3)	0.8212 (2)	−0.20139 (12)	0.0157 (3)
S1	0.48754 (15)	0.92007 (11)	−0.18337 (5)	0.01635 (14)	0.858 (3)
C11	0.4517 (4)	0.9262 (3)	−0.3119 (2)	0.0175 (4)	0.858 (3)
H11A	0.3221	0.9722	−0.3402	0.021*	0.858 (3)
C12	0.6347 (6)	0.8561 (5)	−0.36790 (19)	0.0170 (5)	0.858 (3)
H12A	0.6451	0.8482	−0.4388	0.020*	0.858 (3)
C13	0.8048 (11)	0.7975 (11)	−0.3055 (5)	0.0155 (9)	0.858 (3)
H13A	0.9418	0.7470	−0.3313	0.019*	0.858 (3)
S1X	0.8460 (16)	0.7887 (18)	−0.3169 (7)	0.0142 (14)	0.142 (3)
C11X	0.588 (3)	0.871 (4)	−0.3591 (15)	0.027 (6)*	0.142 (3)
H11B	0.5534	0.8750	−0.4278	0.032*	0.142 (3)
C12X	0.444 (3)	0.928 (2)	−0.2819 (11)	0.016 (3)*	0.142 (3)
H12B	0.3003	0.9781	−0.2906	0.019*	0.142 (3)
C13X	0.536 (3)	0.904 (4)	−0.1870 (14)	0.026 (6)*	0.142 (3)
H13B	0.4656	0.9371	−0.1239	0.031*	0.142 (3)

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
Br1	0.01880 (9)	0.02695 (9)	0.01295 (7)	−0.00228 (6)	−0.00175 (5)	0.00569 (5)
O1	0.0144 (5)	0.0291 (6)	0.0178 (5)	0.0011 (4)	−0.0008 (4)	0.0051 (4)
C1	0.0141 (7)	0.0169 (6)	0.0188 (7)	0.0007 (5)	−0.0024 (5)	0.0019 (5)
C2	0.0142 (7)	0.0160 (6)	0.0231 (7)	0.0001 (5)	0.0014 (5)	0.0034 (5)
C3	0.0177 (7)	0.0179 (7)	0.0181 (7)	0.0019 (5)	0.0014 (5)	0.0048 (5)
C4	0.0153 (7)	0.0175 (6)	0.0138 (6)	0.0025 (5)	−0.0012 (5)	0.0029 (5)
C5	0.0152 (7)	0.0154 (6)	0.0149 (6)	0.0011 (5)	0.0009 (5)	0.0028 (5)
C6	0.0148 (7)	0.0141 (6)	0.0149 (6)	0.0020 (5)	−0.0010 (5)	0.0019 (5)
C7	0.0148 (7)	0.0159 (6)	0.0144 (6)	0.0008 (5)	−0.0020 (5)	0.0018 (5)
C8	0.0156 (7)	0.0186 (7)	0.0151 (6)	0.0034 (5)	−0.0025 (5)	0.0022 (5)
C9	0.0158 (7)	0.0161 (6)	0.0164 (6)	0.0013 (5)	−0.0009 (5)	0.0035 (5)
C10	0.0158 (7)	0.0151 (6)	0.0165 (6)	0.0012 (5)	−0.0001 (5)	0.0033 (5)
S1	0.0142 (3)	0.0188 (3)	0.0159 (2)	0.0030 (2)	0.00010 (18)	0.00280 (16)
C11	0.0183 (10)	0.0190 (9)	0.0156 (10)	−0.0008 (6)	−0.0033 (8)	0.0047 (8)
C12	0.0191 (12)	0.0207 (11)	0.0115 (9)	−0.0016 (10)	−0.0018 (8)	0.0038 (7)
C13	0.010 (2)	0.0156 (14)	0.0203 (17)	0.0011 (14)	0.0046 (12)	0.0013 (11)
S1X	0.009 (3)	0.022 (2)	0.011 (2)	0.007 (2)	0.0016 (18)	0.0037 (15)

Geometric parameters (Å, º)

Br1—C4	1.9022 (15)	C9—H9A	0.9300
O1—C7	1.225 (2)	C10—C13	1.394 (6)
C1—C2	1.391 (2)	C10—C13X	1.407 (15)
C1—C6	1.396 (2)	C10—S1X	1.608 (8)
C1—H1A	0.9300	C10—S1	1.7158 (18)
C2—C3	1.386 (2)	S1—C11	1.714 (3)
C2—H2A	0.9300	C11—C12	1.364 (4)
C3—C4	1.390 (2)	C11—H11A	0.9300
C3—H3A	0.9300	C12—C13	1.398 (7)
C4—C5	1.387 (2)	C12—H12A	0.9300
C5—C6	1.398 (2)	C13—H13A	0.9300
C5—H5A	0.9300	S1X—C11X	1.749 (15)
C6—C7	1.498 (2)	C11X—C12X	1.345 (15)
C7—C8	1.479 (2)	C11X—H11B	0.9300
C8—C9	1.343 (2)	C12X—C13X	1.395 (17)
C8—H8A	0.9300	C12X—H12B	0.9300
C9—C10	1.443 (2)	C13X—H13B	0.9300
C2—C1—C6	120.07 (15)	C13—C10—C9	127.0 (3)
C2—C1—H1A	120.0	C13X—C10—C9	124.0 (8)
C6—C1—H1A	120.0	C13X—C10—S1X	116.1 (8)
C3—C2—C1	120.50 (15)	C9—C10—S1X	119.8 (3)
C3—C2—H2A	119.8	C13—C10—S1	109.3 (3)
C1—C2—H2A	119.8	C9—C10—S1	123.70 (12)
C2—C3—C4	118.73 (15)	S1X—C10—S1	116.5 (3)
C2—C3—H3A	120.6	C11—S1—C10	92.44 (10)
C4—C3—H3A	120.6	C12—C11—S1	112.30 (19)
C5—C4—C3	122.07 (15)	C12—C11—H11A	123.8
C5—C4—Br1	119.54 (12)	S1—C11—H11A	123.8
C3—C4—Br1	118.39 (12)	C11—C12—C13	111.5 (3)
C4—C5—C6	118.57 (15)	C11—C12—H12A	124.2
C4—C5—H5A	120.7	C13—C12—H12A	124.2
C6—C5—H5A	120.7	C10—C13—C12	114.5 (4)
C1—C6—C5	120.03 (14)	C10—C13—H13A	122.8
C1—C6—C7	121.77 (14)	C12—C13—H13A	122.8
C5—C6—C7	118.13 (14)	C10—S1X—C11X	89.5 (7)
O1—C7—C8	122.02 (15)	C12X—C11X—S1X	112.9 (13)
O1—C7—C6	119.78 (14)	C12X—C11X—H11B	123.5
C8—C7—C6	118.20 (14)	S1X—C11X—H11B	123.5
C9—C8—C7	119.71 (15)	C11X—C12X—C13X	111.6 (14)
C9—C8—H8A	120.1	C11X—C12X—H12B	124.2
C7—C8—H8A	120.1	C13X—C12X—H12B	124.2
C8—C9—C10	126.24 (15)	C12X—C13X—C10	109.6 (13)
C8—C9—H9A	116.9	C12X—C13X—H13B	125.2
C10—C9—H9A	116.9	C10—C13X—H13B	125.2
C13—C10—C13X	109.0 (9)
C6—C1—C2—C3	1.6 (2)	C13—C10—S1—C11	0.5 (4)
C1—C2—C3—C4	−0.5 (2)	C9—C10—S1—C11	−179.58 (15)
C2—C3—C4—C5	−0.8 (2)	S1X—C10—S1—C11	2.3 (5)
C2—C3—C4—Br1	179.88 (12)	C10—S1—C11—C12	−0.2 (2)
C3—C4—C5—C6	1.0 (2)	S1—C11—C12—C13	−0.1 (5)
Br1—C4—C5—C6	−179.69 (11)	C13X—C10—C13—C12	−1.2 (14)
C2—C1—C6—C5	−1.4 (2)	C9—C10—C13—C12	179.4 (3)
C2—C1—C6—C7	175.45 (14)	S1X—C10—C13—C12	−168 (7)
C4—C5—C6—C1	0.1 (2)	S1—C10—C13—C12	−0.6 (6)
C4—C5—C6—C7	−176.85 (13)	C11—C12—C13—C10	0.5 (7)
C1—C6—C7—O1	−150.63 (15)	C13—C10—S1X—C11X	10 (6)
C5—C6—C7—O1	26.3 (2)	C13X—C10—S1X—C11X	−3.9 (17)
C1—C6—C7—C8	29.3 (2)	C9—C10—S1X—C11X	178.4 (10)
C5—C6—C7—C8	−153.80 (14)	S1—C10—S1X—C11X	−3.4 (12)
O1—C7—C8—C9	10.9 (2)	C10—S1X—C11X—C12X	3 (2)
C6—C7—C8—C9	−169.04 (14)	S1X—C11X—C12X—C13X	−1 (3)
C7—C8—C9—C10	−176.94 (15)	C11X—C12X—C13X—C10	−2 (3)
C8—C9—C10—C13	−168.2 (4)	C13—C10—C13X—C12X	2 (2)
C8—C9—C10—C13X	12.5 (14)	C9—C10—C13X—C12X	−178.5 (11)
C8—C9—C10—S1X	−170.1 (6)	S1X—C10—C13X—C12X	4 (2)
C8—C9—C10—S1	11.8 (2)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
C9—H9A···O1	0.93	2.47	2.805 (2)	101
C11X—H11B···Br1^i	0.93	2.83	3.486 (19)	128
C2—H2A···Cg1^ii	0.93	2.90	3.544 (2)	128
C2—H2A···Cg2^ii	0.93	2.88	3.536 (9)	128
C5—H5A···Cg1^iii	0.93	2.85	3.561 (2)	134
C5—H5A···Cg2^iii	0.93	2.85	3.553 (8)	133
C9—H9A···Cg3^iv	0.93	3.07	3.633 (2)	121
C11—H11A···Cg3^v	0.93	3.04	3.581 (2)	118
C12X—H12B···Cg3^v	0.93	2.88	3.535 (16)	129

Symmetry codes: (i) x−1, y, z−1; (ii) −x+1, −y+1, −z; (iii) −x+2, −y+2, −z; (iv) −x+2, −y+1, −z; (v) −x+1, −y+2, −z.