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The title compound, C18H15BrO3, was obtained by bromination of phenprocoumone with N-bromo­succin­imide. The X-ray structure confirms an earlier proposal concerning the regioselectivity of the reaction to introduce the Br atom at the 3-position.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536805006124/ob6484sup1.cif
Contains datablocks I, global

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S1600536805006124/ob6484Isup2.hkl
Contains datablock I

CCDC reference: 270497

Key indicators

  • Single-crystal X-ray study
  • T = 295 K
  • Mean [sigma](C-C) = 0.005 Å
  • R factor = 0.041
  • wR factor = 0.115
  • Data-to-parameter ratio = 14.7

checkCIF/PLATON results

No syntax errors found



Alert level C PLAT220_ALERT_2_C Large Non-Solvent C Ueq(max)/Ueq(min) ... 2.51 Ratio PLAT432_ALERT_2_C Short Inter X...Y Contact Br1 .. C5 .. 3.29 Ang.
0 ALERT level A = In general: serious problem 0 ALERT level B = Potentially serious problem 2 ALERT level C = Check and explain 0 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 0 ALERT type 3 Indicator that the structure quality may be low 0 ALERT type 4 Improvement, methodology, query or suggestion

Computing details top

Data collection: COLLECT (Nonius, 1998); cell refinement: COLLECT; data reduction: CORINC (Dräger et al., 1971); program(s) used to solve structure: SIR92 (Altomare et al., 1994); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: ORTEPII (Johnson, 1976); software used to prepare material for publication: SHELXL97.

(3RS,1SR)-3-Bromo-3-(1-phenylpropyl)chroman-2,4-dione top
Crystal data top
C18H15BrO3Z = 2
Mr = 359.21F(000) = 364
Triclinic, P1Dx = 1.540 Mg m3
Hall symbol: -P 1Cu Kα radiation, λ = 1.54178 Å
a = 6.2769 (16) ÅCell parameters from 25 reflections
b = 8.6095 (10) Åθ = 60–71°
c = 14.775 (3) ŵ = 3.70 mm1
α = 91.154 (12)°T = 295 K
β = 90.796 (18)°Plate, colourless
γ = 103.908 (14)°0.38 × 0.28 × 0.02 mm
V = 774.7 (3) Å3
Data collection top
Enraf–Nonius CAD-4
diffractometer
2812 reflections with I > 2σ(I)
Radiation source: rotating anodeRint = 0.043
Graphite monochromatorθmax = 73.1°, θmin = 3.0°
θ/2ω scansh = 77
Absorption correction: numerical
(de Meulenaer & Tompa; 1965)
k = 1010
Tmin = 0.353, Tmax = 0.926l = 180
3234 measured reflections3 standard reflections every 60 min
3109 independent reflections intensity decay: 10%
Refinement top
Refinement on F2Primary atom site location: structure-invariant direct methods
Least-squares matrix: fullSecondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.041Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.115Only H-atom displacement parameters refined
S = 1.12 w = 1/[σ2(Fo2) + (0.0656P)2 + 0.3708P]
where P = (Fo2 + 2Fc2)/3
3109 reflections(Δ/σ)max < 0.001
212 parametersΔρmax = 0.57 e Å3
0 restraintsΔρmin = 0.57 e Å3
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
Br10.02158 (5)0.00819 (4)0.16282 (2)0.05098 (14)
C10.1725 (5)0.2004 (3)0.20421 (18)0.0387 (6)
C20.1484 (5)0.3042 (3)0.12335 (19)0.0418 (6)
C30.2876 (5)0.2931 (3)0.04549 (19)0.0431 (6)
C40.2542 (6)0.3556 (4)0.0385 (2)0.0519 (8)
H40.14100.40690.04650.060 (11)*
C50.3878 (7)0.3416 (4)0.1093 (2)0.0616 (10)
H50.36410.38270.16530.075 (13)*
C60.5586 (7)0.2663 (4)0.0977 (2)0.0640 (10)
H60.64780.25670.14620.072 (13)*
C70.5967 (6)0.2062 (4)0.0157 (2)0.0559 (8)
H70.71180.15670.00770.068 (12)*
C80.4605 (5)0.2204 (4)0.0551 (2)0.0461 (7)
O90.5154 (4)0.1596 (3)0.13657 (15)0.0535 (5)
C100.3974 (5)0.1572 (4)0.2115 (2)0.0446 (6)
O110.0143 (4)0.3837 (3)0.12442 (16)0.0548 (6)
O120.4655 (5)0.1128 (3)0.27981 (17)0.0632 (7)
C130.0904 (5)0.2606 (4)0.29277 (19)0.0445 (6)
H130.05560.27610.27780.049 (9)*
C140.2300 (6)0.4274 (4)0.3190 (2)0.0489 (7)
C150.1457 (8)0.5604 (4)0.3080 (2)0.0620 (10)
H150.00510.54730.28340.069 (13)*
C160.2656 (11)0.7120 (5)0.3328 (3)0.0820 (15)
H160.20520.79950.32470.14 (3)*
C170.4685 (12)0.7338 (6)0.3684 (3)0.0947 (18)
H170.54790.83660.38450.13 (2)*
C180.5608 (10)0.6068 (8)0.3814 (4)0.0970 (17)
H180.70210.62290.40570.11 (2)*
C190.4380 (8)0.4510 (5)0.3571 (3)0.0710 (11)
H190.49770.36360.36690.060 (11)*
C200.0557 (7)0.1456 (5)0.3717 (2)0.0609 (9)
H20A0.01690.03890.34950.090 (11)*
H20B0.19720.14120.39740.090 (11)*
C210.0807 (8)0.1970 (6)0.4444 (2)0.0717 (11)
H21A0.10100.12160.49240.104 (10)*
H21B0.22100.20100.41930.104 (10)*
H21C0.00680.30110.46790.104 (10)*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
Br10.0536 (2)0.03718 (19)0.0596 (2)0.00627 (13)0.00442 (14)0.00108 (13)
C10.0437 (15)0.0335 (13)0.0381 (13)0.0082 (11)0.0023 (11)0.0006 (10)
C20.0475 (16)0.0358 (14)0.0429 (14)0.0119 (12)0.0071 (12)0.0011 (11)
C30.0524 (17)0.0319 (13)0.0409 (14)0.0027 (12)0.0002 (12)0.0033 (10)
C40.066 (2)0.0334 (14)0.0523 (17)0.0049 (13)0.0098 (15)0.0014 (12)
C50.089 (3)0.0446 (18)0.0399 (16)0.0051 (17)0.0029 (16)0.0063 (13)
C60.081 (3)0.052 (2)0.0505 (18)0.0007 (18)0.0181 (18)0.0060 (15)
C70.058 (2)0.0458 (17)0.063 (2)0.0104 (15)0.0075 (16)0.0043 (14)
C80.0547 (18)0.0386 (15)0.0422 (15)0.0058 (12)0.0011 (12)0.0023 (11)
O90.0526 (13)0.0649 (14)0.0504 (12)0.0281 (11)0.0026 (10)0.0063 (10)
C100.0558 (18)0.0399 (15)0.0414 (14)0.0181 (13)0.0026 (12)0.0012 (11)
O110.0630 (14)0.0574 (13)0.0521 (12)0.0306 (11)0.0041 (10)0.0031 (10)
O120.0712 (16)0.0774 (17)0.0523 (13)0.0400 (14)0.0065 (11)0.0085 (12)
C130.0546 (17)0.0407 (15)0.0402 (14)0.0150 (13)0.0066 (12)0.0046 (11)
C140.066 (2)0.0447 (16)0.0370 (14)0.0142 (14)0.0115 (13)0.0011 (11)
C150.100 (3)0.0491 (19)0.0425 (16)0.0286 (19)0.0092 (18)0.0010 (13)
C160.142 (5)0.048 (2)0.057 (2)0.022 (3)0.019 (3)0.0023 (17)
C170.144 (5)0.054 (3)0.074 (3)0.002 (3)0.028 (3)0.016 (2)
C180.081 (3)0.108 (4)0.088 (3)0.002 (3)0.002 (3)0.037 (3)
C190.080 (3)0.067 (2)0.066 (2)0.019 (2)0.006 (2)0.0182 (19)
C200.080 (3)0.057 (2)0.0486 (18)0.0213 (18)0.0122 (17)0.0139 (15)
C210.083 (3)0.091 (3)0.0456 (18)0.026 (2)0.0181 (18)0.0125 (18)
Geometric parameters (Å, º) top
Br1—C11.992 (3)C16—C171.341 (8)
C1—C21.533 (4)C17—C181.370 (9)
C1—C131.538 (4)C18—C191.414 (7)
C1—C101.547 (4)C20—C211.507 (5)
C2—O111.206 (4)C4—H40.9300
C2—C31.469 (4)C5—H50.9300
C3—C81.384 (5)C6—H60.9300
C3—C41.396 (4)C7—H70.9300
C4—C51.371 (5)C13—H130.9800
C5—C61.390 (6)C15—H150.9300
C6—C71.369 (6)C16—H160.9300
C7—C81.382 (5)C17—H170.9300
C8—O91.393 (4)C18—H180.9300
O9—C101.339 (4)C19—H190.9300
C10—O121.195 (4)C20—H20A0.9700
C13—C201.529 (4)C20—H20B0.9700
C13—C141.531 (4)C21—H21A0.9600
C14—C191.383 (6)C21—H21B0.9600
C14—C151.383 (5)C21—H21C0.9600
C15—C161.380 (6)
C2—C1—C13112.7 (2)C21—C20—C13111.6 (3)
C2—C1—C10114.4 (2)C3—C4—H4120.00
C13—C1—C10115.3 (2)C5—C4—H4120.00
C2—C1—Br1100.32 (18)C4—C5—H5120.00
C13—C1—Br1111.1 (2)C6—C5—H5120.00
C10—C1—Br1101.28 (18)C5—C6—H6120.00
O11—C2—C3123.6 (3)C7—C6—H6120.00
O11—C2—C1120.1 (3)C6—C7—H7121.00
C3—C2—C1116.3 (2)C8—C7—H7121.00
C8—C3—C4118.1 (3)C1—C13—H13105.00
C8—C3—C2119.5 (3)C14—C13—H13105.00
C4—C3—C2122.4 (3)C20—C13—H13105.00
C5—C4—C3120.2 (3)C14—C15—H15119.00
C4—C5—C6120.2 (3)C16—C15—H15119.00
C7—C6—C5120.6 (3)C15—C16—H16120.00
C6—C7—C8118.6 (4)C17—C16—H16120.00
C7—C8—C3122.1 (3)C16—C17—H17120.00
C7—C8—O9114.5 (3)C18—C17—H17120.00
C3—C8—O9123.3 (3)C17—C18—H18120.00
C10—O9—C8123.0 (2)C19—C18—H18121.00
O12—C10—O9118.2 (3)C14—C19—H19120.00
O12—C10—C1123.1 (3)C18—C19—H19120.00
O9—C10—C1118.6 (2)C13—C20—H20A109.00
C20—C13—C14113.0 (3)C13—C20—H20B109.00
C20—C13—C1116.7 (3)C21—C20—H20A109.00
C14—C13—C1110.2 (2)C21—C20—H20B109.00
C19—C14—C15117.7 (4)H20A—C20—H20B108.00
C19—C14—C13122.2 (3)C20—C21—H21A109.00
C15—C14—C13120.0 (3)C20—C21—H21B109.00
C16—C15—C14121.4 (5)C20—C21—H21C109.00
C17—C16—C15120.4 (5)H21A—C21—H21B109.00
C16—C17—C18121.0 (5)H21A—C21—H21C109.00
C17—C18—C19119.0 (6)H21B—C21—H21C110.00
C14—C19—C18120.5 (5)
C13—C1—C2—O1123.8 (4)C13—C1—C10—O1227.9 (4)
C10—C1—C2—O11158.0 (3)Br1—C1—C10—O1292.1 (3)
Br1—C1—C2—O1194.5 (3)C2—C1—C10—O923.4 (4)
C13—C1—C2—C3159.3 (3)C13—C1—C10—O9156.5 (3)
C10—C1—C2—C325.0 (4)Br1—C1—C10—O983.5 (3)
Br1—C1—C2—C382.5 (3)C2—C1—C13—C20165.9 (3)
O11—C2—C3—C8169.6 (3)C10—C1—C13—C2060.3 (4)
C1—C2—C3—C813.5 (4)Br1—C1—C13—C2054.2 (3)
O11—C2—C3—C49.4 (5)C2—C1—C13—C1463.5 (3)
C1—C2—C3—C4167.4 (3)C10—C1—C13—C1470.4 (3)
C8—C3—C4—C51.2 (4)Br1—C1—C13—C14175.2 (2)
C2—C3—C4—C5179.7 (3)C20—C13—C14—C1956.0 (4)
C3—C4—C5—C60.5 (5)C1—C13—C14—C1976.6 (4)
C4—C5—C6—C70.4 (5)C20—C13—C14—C15121.5 (3)
C5—C6—C7—C80.7 (5)C1—C13—C14—C15105.9 (3)
C6—C7—C8—C30.1 (5)C19—C14—C15—C161.0 (5)
C6—C7—C8—O9178.4 (3)C13—C14—C15—C16178.6 (3)
C4—C3—C8—C71.0 (5)C14—C15—C16—C170.0 (6)
C2—C3—C8—C7179.9 (3)C15—C16—C17—C180.3 (7)
C4—C3—C8—O9177.3 (3)C16—C17—C18—C190.4 (8)
C2—C3—C8—O91.8 (4)C15—C14—C19—C181.7 (6)
C7—C8—O9—C10177.3 (3)C13—C14—C19—C18179.3 (4)
C3—C8—O9—C104.3 (5)C17—C18—C19—C141.5 (7)
C8—O9—C10—O12174.9 (3)C14—C13—C20—C2166.3 (4)
C8—O9—C10—C19.2 (4)C1—C13—C20—C21164.4 (3)
C2—C1—C10—O12161.0 (3)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
C4—H4···O11i0.932.543.372 (4)150
Symmetry code: (i) x, y+1, z.
 

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