Literature DB >> 21587536

2-(4-Chloro-phen-yl)-6-meth-oxy-chroman-4-one.

Jerry P Jasinski, Albert E Pek, B Narayana, H S Yathirajan, Prakash S Nayak.   

Abstract

In the title mol-ecule, C(16)H(13)Cl O(3), the two aromatic rings form a dihedral angle of 65.3 (1)°. In the crystal structure, weak inter-molecular C-H⋯O hydrogen bonds link the mol-ecules into centrosymmetric dimers, which are further packed into columns propagating in [100] by weak C-H⋯π inter-actions.

Entities:  

Year:  2010        PMID： 21587536      PMCID： PMC2983332          DOI： 10.1107/S1600536810035816

Source DB:  PubMed          Journal:  Acta Crystallogr Sect E Struct Rep Online        ISSN： 1600-5368


Related literature

For the pharmacological and alkyl­ating properties of chromenes (benzopyrans) and their derivatives and for their use as synthons for the synthesis of natural products, see: Brooks (1998 ▶); Chenera et al. (1993 ▶); Ellis et al. (1997 ▶); Gabor et al. (1988 ▶); Hatakeyama et al. (1988 ▶); Hyana & Saimoto, et al. (1987 ▶); Kooijman et al. (1984 ▶); Liu et al. (2007 ▶); Tang et al. (2007 ▶); Valenti et al. (1993 ▶). For related structures, see: Brito et al. (2008 ▶); Butcher et al. (2007 ▶); Li et al. (2007 ▶); Nallasivam et al. (2009 ▶); Hao et al. (2010 ▶). For bond-length data, see: Allen et al. (1987 ▶).

Experimental

Crystal data

C16H13ClO3 M = 288.71 Triclinic, a = 5.0188 (3) Å b = 12.0138 (7) Å c = 12.3708 (7) Å α = 108.035 (5)° β = 98.379 (4)° γ = 91.820 (5)° V = 699.33 (7) Å3 Z = 2 Cu Kα radiation μ = 2.46 mm−1 T = 293 K 0.40 × 0.35 × 0.20 mm

Data collection

Oxford Diffraction Xcalibur diffractometer with a Ruby (Gemini Cu) detector Absorption correction: multi-scan (CrysAlis RED; Oxford Diffraction, 2007 ▶) T min = 0.590, T max = 1.000 4431 measured reflections 2733 independent reflections 2318 reflections with I > 2σ(I) R int = 0.018

Refinement

R[F 2 > 2σ(F 2)] = 0.049 wR(F 2) = 0.156 S = 1.62 2733 reflections 183 parameters H-atom parameters constrained Δρmax = 0.17 e Å−3 Δρmin = −0.39 e Å−3 Data collection: CrysAlis PRO (Oxford Diffraction, 2007 ▶); cell refinement: CrysAlis RED (Oxford Diffraction, 2007 ▶); data reduction: CrysAlis RED; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: SHELXTL (Sheldrick, 2008 ▶); software used to prepare material for publication: PLATON (Spek, 2009 ▶). Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536810035816/cv2754sup1.cif Structure factors: contains datablocks I. DOI: 10.1107/S1600536810035816/cv2754Isup2.hkl Additional supplementary materials: crystallographic information; 3D view; checkCIF report
C16H13ClO3Z = 2
Mr = 288.71F(000) = 300
Triclinic, P1Dx = 1.371 Mg m−3
Hall symbol: -P 1Cu Kα radiation, λ = 1.54178 Å
a = 5.0188 (3) ÅCell parameters from 2808 reflections
b = 12.0138 (7) Åθ = 4.5–74.2°
c = 12.3708 (7) ŵ = 2.46 mm−1
α = 108.035 (5)°T = 293 K
β = 98.379 (4)°Block, colourless
γ = 91.820 (5)°0.40 × 0.35 × 0.20 mm
V = 699.33 (7) Å3
Oxford Diffraction Xcalibur with a Ruby (Gemini Cu) detector diffractometer2733 independent reflections
Radiation source: Enhance (Cu) X-ray Source2318 reflections with I > 2σ(I)
graphiteRint = 0.018
Detector resolution: 10.5081 pixels mm-1θmax = 74.3°, θmin = 4.5°
ω scansh = −6→5
Absorption correction: multi-scan (CrysAlis RED; Oxford Diffraction, 2007)k = −14→14
Tmin = 0.590, Tmax = 1.000l = −13→15
4431 measured reflections
Refinement on F2Primary atom site location: structure-invariant direct methods
Least-squares matrix: fullSecondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.049Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.156H-atom parameters constrained
S = 1.62w = 1/[σ2(Fo2) + (0.072P)2] where P = (Fo2 + 2Fc2)/3
2733 reflections(Δ/σ)max < 0.001
183 parametersΔρmax = 0.17 e Å−3
0 restraintsΔρmin = −0.39 e Å−3
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.
xyzUiso*/Ueq
Cl11.44159 (18)1.09772 (6)1.41015 (7)0.1128 (4)
C150.1890 (4)0.52826 (16)0.74092 (15)0.0510 (4)
H140.18710.44690.72050.061*
C100.3876 (3)0.59907 (15)0.82937 (14)0.0445 (4)
C110.3896 (3)0.72078 (15)0.85979 (14)0.0457 (4)
C50.8624 (4)0.83325 (15)1.12894 (15)0.0486 (4)
C41.0438 (4)0.90581 (17)1.10279 (18)0.0588 (5)
H41.04510.90041.02620.071*
C31.2237 (5)0.98652 (19)1.1888 (2)0.0698 (6)
H31.34421.03561.17060.084*
C21.2221 (5)0.99320 (18)1.3011 (2)0.0703 (6)
C60.8664 (5)0.8411 (2)1.24293 (19)0.0714 (6)
H60.74590.79241.26170.098 (9)*
C11.0475 (6)0.9205 (2)1.3295 (2)0.0830 (7)
H11.05100.92471.40610.100*
C120.1994 (4)0.77156 (17)0.79994 (16)0.0547 (4)
H110.20340.85280.81830.066*
C14−0.0029 (4)0.57890 (18)0.68435 (16)0.0564 (5)
C130.0067 (4)0.70101 (19)0.71392 (17)0.0610 (5)
H12−0.12040.73520.67440.073*
C70.6684 (3)0.74364 (14)1.03660 (15)0.0454 (4)
H70.51490.72471.07030.055*
C90.5995 (3)0.54557 (14)0.88808 (15)0.0453 (4)
C80.7957 (3)0.63138 (15)0.98271 (15)0.0483 (4)
H8B0.85680.59581.04150.058*
H8A0.95210.64970.95170.058*
O10.5707 (2)0.79532 (10)0.94837 (11)0.0500 (3)
O20.6175 (3)0.43987 (11)0.86011 (12)0.0597 (4)
O3−0.2094 (3)0.51981 (15)0.59887 (13)0.0759 (5)
C16−0.2392 (5)0.3957 (2)0.5693 (2)0.0841 (7)
H15A−0.07930.36350.54250.126*
H15B−0.39240.36520.50940.126*
H15C−0.26610.37450.63580.126*
U11U22U33U12U13U23
Cl10.1341 (7)0.0652 (4)0.1049 (5)−0.0140 (4)−0.0625 (5)0.0169 (3)
C150.0503 (10)0.0501 (9)0.0500 (9)0.0020 (7)0.0083 (8)0.0124 (8)
C100.0406 (8)0.0485 (9)0.0462 (9)0.0040 (7)0.0085 (7)0.0170 (7)
C110.0419 (8)0.0491 (9)0.0480 (9)0.0028 (7)0.0056 (7)0.0192 (7)
C50.0470 (9)0.0455 (9)0.0520 (9)0.0090 (7)0.0023 (7)0.0157 (7)
C40.0606 (11)0.0546 (11)0.0586 (11)−0.0020 (9)0.0036 (9)0.0181 (9)
C30.0647 (13)0.0559 (11)0.0834 (15)−0.0077 (9)−0.0067 (11)0.0239 (10)
C20.0761 (14)0.0470 (10)0.0716 (13)0.0032 (9)−0.0259 (11)0.0129 (9)
C60.0796 (15)0.0738 (14)0.0572 (12)−0.0087 (11)0.0004 (10)0.0222 (10)
C10.1029 (19)0.0826 (16)0.0531 (12)−0.0017 (14)−0.0109 (12)0.0182 (11)
C120.0571 (11)0.0532 (10)0.0569 (10)0.0092 (8)0.0031 (8)0.0242 (8)
C140.0500 (10)0.0679 (12)0.0459 (9)0.0011 (8)0.0007 (7)0.0139 (8)
C130.0573 (11)0.0707 (12)0.0551 (10)0.0127 (9)−0.0032 (9)0.0251 (9)
C70.0432 (9)0.0458 (9)0.0496 (9)0.0051 (7)0.0050 (7)0.0194 (7)
C90.0425 (9)0.0446 (9)0.0515 (9)0.0056 (7)0.0108 (7)0.0175 (7)
C80.0414 (9)0.0490 (9)0.0555 (10)0.0071 (7)0.0040 (7)0.0195 (8)
O10.0508 (7)0.0434 (6)0.0553 (7)0.0009 (5)−0.0033 (5)0.0206 (5)
O20.0647 (8)0.0437 (7)0.0688 (8)0.0083 (6)0.0041 (6)0.0182 (6)
O30.0662 (9)0.0812 (11)0.0629 (9)−0.0018 (7)−0.0170 (7)0.0113 (8)
C160.0807 (16)0.0814 (16)0.0677 (14)−0.0132 (13)−0.0115 (12)0.0041 (12)
Cl1—C21.744 (2)C1—H10.9300
C15—C141.376 (3)C12—C131.370 (3)
C15—C101.402 (2)C12—H110.9300
C15—H140.9300C14—O31.366 (2)
C10—C111.392 (2)C14—C131.395 (3)
C10—C91.476 (2)C13—H120.9300
C11—O11.371 (2)C7—O11.449 (2)
C11—C121.393 (2)C7—C81.515 (2)
C5—C61.381 (3)C7—H70.9800
C5—C41.380 (3)C9—O21.219 (2)
C5—C71.503 (2)C9—C81.502 (2)
C4—C31.383 (3)C8—H8B0.9700
C4—H40.9300C8—H8A0.9700
C3—C21.367 (4)O3—C161.418 (3)
C3—H30.9300C16—H15A0.9600
C2—C11.373 (4)C16—H15B0.9600
C6—C11.383 (3)C16—H15C0.9600
C6—H60.9300
C14—C15—C10120.12 (17)C15—C14—O3125.69 (19)
C14—C15—H14119.9C15—C14—C13119.31 (17)
C10—C15—H14119.9O3—C14—C13115.00 (18)
C11—C10—C15119.75 (16)C12—C13—C14121.37 (17)
C11—C10—C9119.71 (15)C12—C13—H12119.3
C15—C10—C9120.51 (15)C14—C13—H12119.3
O1—C11—C10122.90 (15)O1—C7—C5108.13 (13)
O1—C11—C12117.23 (15)O1—C7—C8109.43 (14)
C10—C11—C12119.86 (16)C5—C7—C8112.84 (14)
C6—C5—C4118.74 (19)O1—C7—H7108.8
C6—C5—C7119.48 (18)C5—C7—H7108.8
C4—C5—C7121.74 (16)C8—C7—H7108.8
C5—C4—C3120.9 (2)O2—C9—C10122.50 (16)
C5—C4—H4119.5O2—C9—C8122.51 (16)
C3—C4—H4119.5C10—C9—C8114.97 (14)
C2—C3—C4119.2 (2)C7—C8—C9111.46 (14)
C2—C3—H3120.4C7—C8—H8B109.3
C4—C3—H3120.4C9—C8—H8B109.3
C3—C2—C1121.2 (2)C7—C8—H8A109.3
C3—C2—Cl1119.3 (2)C9—C8—H8A109.3
C1—C2—Cl1119.45 (19)H8B—C8—H8A108.0
C5—C6—C1120.8 (2)C11—O1—C7112.96 (12)
C5—C6—H6119.6C14—O3—C16117.73 (18)
C1—C6—H6119.6O3—C16—H15A109.5
C2—C1—C6119.1 (2)O3—C16—H15B109.5
C2—C1—H1120.4H15A—C16—H15B109.5
C6—C1—H1120.4O3—C16—H15C109.5
C13—C12—C11119.55 (18)H15A—C16—H15C109.5
C13—C12—H11120.2H15B—C16—H15C109.5
C11—C12—H11120.2
C14—C15—C10—C110.1 (3)C15—C14—C13—C12−1.5 (3)
C14—C15—C10—C9−178.06 (16)O3—C14—C13—C12178.56 (19)
C15—C10—C11—O1177.30 (15)C6—C5—C7—O1142.77 (18)
C9—C10—C11—O1−4.6 (2)C4—C5—C7—O1−39.4 (2)
C15—C10—C11—C12−1.9 (3)C6—C5—C7—C8−96.0 (2)
C9—C10—C11—C12176.21 (15)C4—C5—C7—C881.8 (2)
C6—C5—C4—C3−1.1 (3)C11—C10—C9—O2−175.33 (17)
C7—C5—C4—C3−178.99 (18)C15—C10—C9—O22.8 (3)
C5—C4—C3—C20.6 (3)C11—C10—C9—C83.1 (2)
C4—C3—C2—C10.7 (4)C15—C10—C9—C8−178.80 (15)
C4—C3—C2—Cl1−178.13 (16)O1—C7—C8—C9−57.54 (18)
C4—C5—C6—C10.4 (3)C5—C7—C8—C9−177.98 (14)
C7—C5—C6—C1178.3 (2)O2—C9—C8—C7−154.04 (17)
C3—C2—C1—C6−1.4 (4)C10—C9—C8—C727.6 (2)
Cl1—C2—C1—C6177.40 (19)C10—C11—O1—C7−26.7 (2)
C5—C6—C1—C20.9 (4)C12—C11—O1—C7152.50 (16)
O1—C11—C12—C13−177.23 (17)C5—C7—O1—C11−179.56 (13)
C10—C11—C12—C132.0 (3)C8—C7—O1—C1157.17 (18)
C10—C15—C14—O3−178.47 (18)C15—C14—O3—C163.6 (3)
C10—C15—C14—C131.6 (3)C13—C14—O3—C16−176.6 (2)
C11—C12—C13—C14−0.3 (3)
Cg1 is the centroid of the C7–C12 ring.
D—H···AD—HH···AD···AD—H···A
C7—H7···O2i0.982.503.260 (2)135
C8—H8B···Cg1ii0.972.693.5709 (18)151
Table 1

Hydrogen-bond geometry (Å, °)

Cg1 is the centroid of the C7–C12 ring.

D—H⋯AD—HH⋯AD⋯AD—H⋯A
C7—H7⋯O2i0.982.503.260 (2)135
C8—H8B⋯Cg1ii0.972.693.5709 (18)151

Symmetry codes: (i) ; (ii) .

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