2-Bromo-1-(4-methyl­phen­yl)-3-[4-(methyl­sulfan­yl)phen­yl]prop-2-en-1-one

Butcher, R.J.; Yathirajan, H.S.; Anilkumar, H.G.; Sarojini, B.K.; Narayana, B.

doi:10.1107/S1600536806011160

2-Bromo-1-(4-methylphenyl)-3-[4-(methylsulfanyl)phenyl]prop-2-en-1-one

R. J. Butcher, H. S. Yathirajan, H. G. Anilkumar, B. K. Sarojini and B. Narayana

The title compound, C₁₇H₁₅BrOS, crystallizes in a non-centrosymmetric space group and shows significant nonlinear optical activity.

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Supporting information

	Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536806011160/hg2019sup1.cif Contains datablocks global, I
	Structure factor file (CIF format) https://doi.org/10.1107/S1600536806011160/hg2019Isup2.hkl Contains datablock I

CCDC reference: 605082

checkCIF report

Key indicators

Single-crystal X-ray study
T = 366 K
Mean (C-C) = 0.003 Å
R factor = 0.024
wR factor = 0.054
Data-to-parameter ratio = 22.0

checkCIF/PLATON results

No syntax errors found



Alert level A
PLAT029_ALERT_3_A _diffrn_measured_fraction_theta_full Low .......       0.93

Author Response: Data was collected out to a 2-theta value of 61.5\%. However, due to the shape of the detector the final shell was not complete. Data was complete to d = 0.75.


Alert level B
PLAT431_ALERT_2_B Short Inter HL..A Contact  Br     ..  S       ..       3.27 Ang.

Alert level C
PLAT063_ALERT_3_C Crystal Probably too Large for Beam Size .......       0.65 mm
PLAT094_ALERT_2_C Ratio of Maximum / Minimum Residual Density ....       2.26

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           30.75
           From the CIF: _reflns_number_total               4028
           Count of symmetry unique reflns         2512
           Completeness (_total/calc)            160.35%
           TEST3: Check Friedels for noncentro structure
           Estimate of Friedel pairs measured      1516
           Fraction of Friedel pairs measured     0.604
           Are heavy atom types Z>Si present        yes

   1 ALERT level A = In general: serious problem
   1 ALERT level B = Potentially serious problem
   2 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
   2 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: SMART (Bruker, 1998); cell refinement: SAINT-Plus (Bruker, 1999); data reduction: SAINT-Plus; program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: SHELXTL (Sheldrick, 1997); software used to prepare material for publication: SHELXTL.

2-Bromo-1-(4-methylphenyl)-3-[4-(methylsulfanyl)phenyl]prop-2-en-1-one top

Crystal data top

C₁₇H₁₅BrOS	F(000) = 352
M_r = 347.26	D_x = 1.564 Mg m⁻³
Monoclinic, P2₁	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: P 2yb	Cell parameters from 6302 reflections
a = 7.9708 (9) Å	θ = 2.4–30.5°
b = 5.5031 (6) Å	µ = 2.92 mm⁻¹
c = 16.9923 (18) Å	T = 366 K
β = 98.291 (2)°	Chunk, colorless
V = 737.56 (14) Å³	0.65 × 0.30 × 0.25 mm
Z = 2

Data collection top

Bruker SMART CCD area-detector diffractometer	4028 independent reflections
Radiation source: fine-focus sealed tube	3821 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.022
φ and ω scans	θ_max = 30.8°, θ_min = 2.4°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	h = −9→11
T_min = 0.230, T_max = 0.482	k = −7→7
8184 measured reflections	l = −24→24

Refinement top

Refinement on F²	Secondary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F² > 2σ(F²)] = 0.024	H-atom parameters constrained
wR(F²) = 0.055	w = 1/[σ²(F_o²)] where P = (F_o² + 2F_c²)/3
S = 0.95	(Δ/σ)_max = 0.002
4028 reflections	Δρ_max = 1.17 e Å⁻³
183 parameters	Δρ_min = −0.52 e Å⁻³
1 restraint	Absolute structure: Flack (1983)
Primary atom site location: structure-invariant direct methods	Absolute structure parameter: 0.029 (6)

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

	x	y	z	U_iso*/U_eq
Br	0.96840 (2)	−0.00274 (4)	0.775087 (9)	0.01950 (5)
S	0.70913 (6)	0.13574 (8)	1.17103 (3)	0.01365 (9)
O	0.9237 (2)	0.3919 (3)	0.64877 (8)	0.0249 (3)
C1	0.5891 (3)	0.3869 (4)	1.20207 (11)	0.0174 (4)
H1A	0.5657	0.3585	1.2552	0.026*
H1B	0.4843	0.4019	1.1667	0.026*
H1C	0.6534	0.5340	1.2009	0.026*
C2	0.7288 (3)	0.2139 (3)	1.07225 (10)	0.0128 (4)
C3	0.8147 (2)	0.0511 (3)	1.02957 (11)	0.0147 (4)
H3A	0.8639	−0.0869	1.0547	0.018*
C4	0.8282 (3)	0.0916 (3)	0.94990 (11)	0.0150 (4)
H4A	0.8862	−0.0191	0.9225	0.018*
C5	0.7544 (2)	0.2997 (3)	0.91034 (11)	0.0129 (4)
C6	0.6733 (2)	0.4639 (4)	0.95536 (10)	0.0136 (4)
H6A	0.6263	0.6045	0.9310	0.016*
C7	0.6604 (3)	0.4248 (3)	1.03493 (11)	0.0144 (4)
H7A	0.6065	0.5383	1.0632	0.017*
C8	0.7491 (2)	0.3614 (3)	0.82629 (10)	0.0133 (4)
H8A	0.6812	0.4957	0.8111	0.016*
C9	0.8206 (3)	0.2674 (4)	0.76608 (11)	0.0151 (4)
C10	0.8046 (3)	0.3912 (4)	0.68660 (11)	0.0170 (4)
C11	0.6408 (2)	0.5098 (5)	0.65509 (9)	0.0138 (3)
C12	0.4857 (3)	0.4050 (3)	0.66474 (11)	0.0149 (4)
H12A	0.4840	0.2640	0.6948	0.018*
C13	0.3341 (2)	0.5077 (5)	0.63022 (9)	0.0164 (3)
H13A	0.2321	0.4324	0.6359	0.020*
C14	0.3334 (3)	0.7240 (4)	0.58690 (11)	0.0167 (4)
C15	0.4891 (3)	0.8284 (4)	0.57676 (11)	0.0172 (4)
H15A	0.4905	0.9712	0.5476	0.021*
C16	0.6410 (3)	0.7230 (4)	0.60942 (11)	0.0158 (4)
H16A	0.7432	0.7932	0.6012	0.019*
C17	0.1689 (3)	0.8443 (5)	0.55354 (12)	0.0253 (5)
H17A	0.0765	0.7352	0.5576	0.038*
H17B	0.1707	0.8848	0.4987	0.038*
H17C	0.1544	0.9897	0.5831	0.038*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
Br	0.01835 (9)	0.02282 (9)	0.01760 (8)	0.00999 (10)	0.00354 (6)	−0.00004 (9)
S	0.0157 (2)	0.0116 (2)	0.01356 (19)	−0.00033 (18)	0.00202 (16)	0.00133 (16)
O	0.0159 (8)	0.0399 (9)	0.0206 (7)	0.0044 (7)	0.0080 (6)	0.0050 (6)
C1	0.0208 (11)	0.0153 (9)	0.0169 (9)	0.0009 (8)	0.0060 (8)	0.0001 (7)
C2	0.0110 (9)	0.0152 (9)	0.0123 (8)	−0.0024 (7)	0.0018 (7)	0.0004 (6)
C3	0.0132 (9)	0.0118 (10)	0.0185 (8)	0.0024 (6)	0.0008 (7)	0.0018 (6)
C4	0.0134 (10)	0.0124 (8)	0.0197 (9)	0.0028 (7)	0.0047 (7)	0.0010 (7)
C5	0.0089 (9)	0.0139 (9)	0.0159 (8)	0.0005 (7)	0.0016 (7)	0.0011 (7)
C6	0.0113 (8)	0.0120 (10)	0.0173 (7)	0.0018 (7)	0.0017 (6)	0.0013 (7)
C7	0.0140 (10)	0.0126 (9)	0.0167 (8)	0.0007 (7)	0.0030 (7)	−0.0016 (6)
C8	0.0115 (9)	0.0113 (8)	0.0169 (8)	0.0024 (7)	0.0016 (7)	0.0028 (7)
C9	0.0111 (9)	0.0179 (9)	0.0160 (8)	0.0032 (7)	0.0013 (7)	0.0008 (7)
C10	0.0148 (10)	0.0203 (9)	0.0157 (8)	−0.0007 (8)	0.0021 (7)	−0.0007 (7)
C11	0.0149 (8)	0.0156 (8)	0.0115 (6)	0.0001 (9)	0.0035 (6)	−0.0010 (9)
C12	0.0164 (10)	0.0134 (8)	0.0153 (8)	−0.0009 (7)	0.0043 (7)	−0.0002 (7)
C13	0.0140 (8)	0.0177 (8)	0.0177 (7)	−0.0037 (10)	0.0025 (6)	−0.0027 (10)
C14	0.0183 (11)	0.0194 (10)	0.0120 (8)	0.0035 (8)	0.0006 (7)	−0.0017 (7)
C15	0.0226 (11)	0.0160 (9)	0.0131 (8)	0.0005 (8)	0.0031 (7)	0.0016 (7)
C16	0.0166 (10)	0.0153 (9)	0.0161 (8)	−0.0028 (8)	0.0039 (7)	−0.0001 (7)
C17	0.0213 (12)	0.0312 (12)	0.0221 (10)	0.0068 (10)	−0.0015 (8)	0.0028 (9)

Geometric parameters (Å, º) top

Br—C9	1.889 (2)	C8—C9	1.344 (2)
S—C2	1.7613 (18)	C8—H8A	0.9300
S—C1	1.803 (2)	C9—C10	1.502 (3)
O—C10	1.220 (2)	C10—C11	1.489 (3)
C1—H1A	0.9600	C11—C12	1.395 (3)
C1—H1B	0.9600	C11—C16	1.407 (3)
C1—H1C	0.9600	C12—C13	1.385 (3)
C2—C3	1.393 (2)	C12—H12A	0.9300
C2—C7	1.395 (3)	C13—C14	1.399 (3)
C3—C4	1.391 (3)	C13—H13A	0.9300
C3—H3A	0.9300	C14—C15	1.401 (3)
C4—C5	1.412 (3)	C14—C17	1.505 (3)
C4—H4A	0.9300	C15—C16	1.385 (3)
C5—C6	1.401 (3)	C15—H15A	0.9300
C5—C8	1.463 (2)	C16—H16A	0.9300
C6—C7	1.388 (2)	C17—H17A	0.9600
C6—H6A	0.9300	C17—H17B	0.9600
C7—H7A	0.9300	C17—H17C	0.9600

C2—S—C1	102.45 (9)	C8—C9—Br	124.68 (15)
S—C1—H1A	109.5	C10—C9—Br	113.62 (13)
S—C1—H1B	109.5	O—C10—C11	121.15 (17)
H1A—C1—H1B	109.5	O—C10—C9	120.26 (19)
S—C1—H1C	109.5	C11—C10—C9	118.59 (17)
H1A—C1—H1C	109.5	C12—C11—C16	118.78 (18)
H1B—C1—H1C	109.5	C12—C11—C10	121.5 (2)
C3—C2—C7	119.17 (16)	C16—C11—C10	119.55 (18)
C3—C2—S	117.20 (14)	C13—C12—C11	120.99 (19)
C7—C2—S	123.61 (14)	C13—C12—H12A	119.5
C4—C3—C2	121.06 (17)	C11—C12—H12A	119.5
C4—C3—H3A	119.5	C12—C13—C14	120.48 (19)
C2—C3—H3A	119.5	C12—C13—H13A	119.8
C3—C4—C5	120.53 (17)	C14—C13—H13A	119.8
C3—C4—H4A	119.7	C13—C14—C15	118.51 (18)
C5—C4—H4A	119.7	C13—C14—C17	120.65 (19)
C6—C5—C4	117.16 (16)	C15—C14—C17	120.83 (19)
C6—C5—C8	115.64 (16)	C16—C15—C14	121.20 (18)
C4—C5—C8	127.18 (17)	C16—C15—H15A	119.4
C7—C6—C5	122.46 (18)	C14—C15—H15A	119.4
C7—C6—H6A	118.8	C15—C16—C11	119.99 (19)
C5—C6—H6A	118.8	C15—C16—H16A	120.0
C6—C7—C2	119.55 (17)	C11—C16—H16A	120.0
C6—C7—H7A	120.2	C14—C17—H17A	109.5
C2—C7—H7A	120.2	C14—C17—H17B	109.5
C9—C8—C5	134.27 (18)	H17A—C17—H17B	109.5
C9—C8—H8A	112.9	C14—C17—H17C	109.5
C5—C8—H8A	112.9	H17A—C17—H17C	109.5
C8—C9—C10	121.31 (18)	H17B—C17—H17C	109.5

C1—S—C2—C3	−178.89 (16)	Br—C9—C10—O	−30.8 (3)
C1—S—C2—C7	−0.30 (19)	C8—C9—C10—C11	−38.2 (3)
C7—C2—C3—C4	−2.2 (3)	Br—C9—C10—C11	148.63 (16)
S—C2—C3—C4	176.44 (16)	O—C10—C11—C12	140.4 (2)
C2—C3—C4—C5	−0.1 (3)	C9—C10—C11—C12	−39.0 (3)
C3—C4—C5—C6	2.0 (3)	O—C10—C11—C16	−34.8 (3)
C3—C4—C5—C8	−176.37 (19)	C9—C10—C11—C16	145.81 (18)
C4—C5—C6—C7	−1.7 (3)	C16—C11—C12—C13	0.0 (3)
C8—C5—C6—C7	176.86 (18)	C10—C11—C12—C13	−175.25 (18)
C5—C6—C7—C2	−0.6 (3)	C11—C12—C13—C14	−2.1 (3)
C3—C2—C7—C6	2.5 (3)	C12—C13—C14—C15	2.4 (3)
S—C2—C7—C6	−176.05 (15)	C12—C13—C14—C17	−176.25 (18)
C6—C5—C8—C9	173.5 (2)	C13—C14—C15—C16	−0.7 (3)
C4—C5—C8—C9	−8.1 (4)	C17—C14—C15—C16	177.91 (18)
C5—C8—C9—C10	−173.3 (2)	C14—C15—C16—C11	−1.3 (3)
C5—C8—C9—Br	−0.9 (3)	C12—C11—C16—C15	1.7 (3)
C8—C9—C10—O	142.4 (2)	C10—C11—C16—C15	177.00 (17)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C13—H13A···Oⁱ	0.93	2.51	3.392 (2)	159
C17—H17B···Oⁱⁱ	0.96	2.51	3.420 (3)	158

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

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2-Bromo-1-(4-methyl­phen­yl)-3-[4-(methyl­sulfan­yl)phen­yl]prop-2-en-1-one

Supporting information

Key indicators

checkCIF/PLATON results

2-Bromo-1-(4-methylphenyl)-3-[4-(methylsulfanyl)phenyl]prop-2-en-1-one