Buy article online - an online subscription or single-article purchase is required to access this article.
Download citation
Download citation
link to html
The mol­ecular structure of the title acid, C15H14O2, exhibits a trans-planar arrangement of the aromatic rings. The carboxyl group is inclined at an angle of 6.4 (1)° with respect to the attached benzene ring. The classical hydrogen-bonded carboxylic acid dimers (O...O = 2.7 Å), characterized by an R22(8) pattern, predominantly stabilize the supramolecular assembly.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536805023329/rz6107sup1.cif
Contains datablocks global, I

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S1600536805023329/rz6107Isup2.hkl
Contains datablock I

CCDC reference: 282621

Key indicators

  • Single-crystal X-ray study
  • T = 293 K
  • Mean [sigma](C-C) = 0.002 Å
  • R factor = 0.038
  • wR factor = 0.114
  • Data-to-parameter ratio = 11.1

checkCIF/PLATON results

No syntax errors found



Alert level A PLAT027_ALERT_3_A _diffrn_reflns_theta_full (too) Low ............ 23.00 Deg.
Author Response: for Compound-I: Due to the difficulties in obtaining suitable crystals, the reported = data set was the best that could be obtained, which yielded the high-quality model.

Alert level B THETM01_ALERT_3_B The value of sine(theta_max)/wavelength is less than 0.575 Calculated sin(theta_max)/wavelength = 0.5554 PLAT023_ALERT_3_B Resolution (too) Low [sin(th)/Lambda < 0.6]..... 23.25 Deg.
Alert level C PLAT143_ALERT_4_C su on c - Axis Small or Missing (x 100000) ..... 10 Ang. PLAT199_ALERT_1_C Check the Reported _cell_measurement_temperature 293 K PLAT200_ALERT_1_C Check the Reported _diffrn_ambient_temperature . 293 K PLAT230_ALERT_2_C Hirshfeld Test Diff for C14 - C15 .. 6.74 su PLAT355_ALERT_3_C Long O-H Bond (0.82A) O2 - H2A ... 1.03 Ang.
1 ALERT level A = In general: serious problem 2 ALERT level B = Potentially serious problem 5 ALERT level C = Check and explain 0 ALERT level G = General alerts; check 2 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

Computing details top

Data collection: SMART (Bruker, 1998); cell refinement: SAINT-Plus (Bruker, 2001); data reduction: SAINT-Plus; program(s) used to solve structure: SHELXS86 (Sheldrick, 1985); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: ORTEP-3 (Farrugia, 1997) and PLATON (Spek, 2003); software used to prepare material for publication: WinGX (Farrugia, 1999) and PARST (Nardelli, 1995).

2-(2-phenylethyl)benzoic acid top
Crystal data top
C15H14O2F(000) = 480
Mr = 226.26Dx = 1.227 Mg m3
Monoclinic, P21/cMo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybcCell parameters from 1036 reflections
a = 13.7005 (2) Åθ = 5–35°
b = 6.0509 (1) ŵ = 0.08 mm1
c = 15.1789 (1) ÅT = 293 K
β = 103.155 (1)°Block, colorless
V = 1225.32 (3) Å30.14 × 0.12 × 0.08 mm
Z = 4
Data collection top
Siemens SMART CCD area-detector
diffractometer
1421 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tubeRint = 0.024
Graphite monochromatorθmax = 23.3°, θmin = 1.5°
ω scansh = 1514
4864 measured reflectionsk = 66
1761 independent reflectionsl = 1614
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)] = 0.038H atoms treated by a mixture of independent and constrained refinement
wR(F2) = 0.114 w = 1/[σ2(Fo2) + (0.0746P)2]
where P = (Fo2 + 2Fc2)/3
S = 1.08(Δ/σ)max = 0.001
1761 reflectionsΔρmax = 0.18 e Å3
159 parametersΔρmin = 0.13 e Å3
0 restraintsExtinction correction: SHELXL97, Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4
Primary atom site location: structure-invariant direct methodsExtinction coefficient: 0.030 (4)
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.

Weighted least-squares planes through the starred atoms (Nardelli, Musatti, Domiano & Andreetti Ric·Sci.(1965),15(II—A),807). Equation of the plane: m1*X+m2*Y+m3*Z=3Dd

Plane 1 m1 =three-dimensional 0.81475(0.00027) m2 =three-dimensional 0.55287(0.00037) m3 =three-dimensional -0.17473(0.00046) D =three-dimensional 5.70407(0.00804) Atom d s d/s (d/s)**2 C8 * -0.0196 0.0016 - 12.655 160.161 C9 * 0.0129 0.0015 8.414 70.798 C10 * 0.0133 0.0018 7.501 56.263 C11 * 0.0083 0.0018 4.559 20.786 C12 * -0.0108 0.0017 - 6.252 39.086 C13 * -0.0125 0.0016 - 7.683 59.025 C14 * -0.0027 0.0014 - 1.924 3.703 C15 * 0.0122 0.0015 8.248 68.027 C7 - 1.4553 0.0016 - 926.059 857586.125 O1 - 0.0969 0.0011 - 85.847 7369.701 O2 0.1484 0.0011 129.301 16718.660 = =three-dimensional=three-dimensional=three-dimensional=three-dimensional=three-dimensional=three-dimensional=three-dimensional=three-dimensional=three-dimensional=three-dimensional=three-dimensional=three-dimensional Sum((d/s)**2) for starred atoms 477.849 Chi-squared at 95% for 5 degrees of freedom: 11.10 The group of atoms deviates significantly from planarity

Plane 2 m1 =three-dimensional 0.77285(0.00044) m2 =three-dimensional 0.57099(0.00060) m3 =three-dimensional -0.27690(0.00068) D =three-dimensional 3.80259(0.01219) Atom d s d/s (d/s)**2 C14 * -0.0002 0.0014 - 0.125 0.016 C15 * 0.0007 0.0015 0.441 0.195 O1 * -0.0001 0.0011 - 0.126 0.016 O2 * -0.0001 0.0011 - 0.112 0.013 C9 0.1543 0.0015 100.862 10173.091 C13 - 0.1415 0.0016 - 86.577 7495.664 = =three-dimensional=three-dimensional=three-dimensional=three-dimensional=three-dimensional=three-dimensional=three-dimensional=three-dimensional=three-dimensional=three-dimensional=three-dimensional=three-dimensional Sum((d/s)**2) for starred atoms 0.239 Chi-squared at 95% for 1 degrees of freedom: 3.84 The group of atoms does not deviate significantly from planarity

Plane 3 m1 =three-dimensional 0.81183(0.00039) m2 =three-dimensional 0.52937(0.00061) m3 =three-dimensional -0.24637(0.00044) D =three-dimensional 3.26026(0.00552) Atom d s d/s (d/s)**2 C1 * 0.0126 0.0018 7.061 49.853 C2 * 0.0005 0.0019 0.254 0.065 C3 * -0.0175 0.0019 - 8.986 80.752 C4 * -0.0048 0.0018 - 2.621 6.868 C5 * 0.0140 0.0016 8.803 77.500 C6 * 0.0045 0.0014 3.174 10.076 C7 * -0.0143 0.0016 - 9.102 82.852 C8 1.3776 0.0015 888.868 790085.500 = =three-dimensional=three-dimensional=three-dimensional=three-dimensional=three-dimensional=three-dimensional=three-dimensional=three-dimensional=three-dimensional=three-dimensional=three-dimensional=three-dimensional Sum((d/s)**2) for starred atoms 307.966 Chi-squared at 95% for 4 degrees of freedom: 9.49 The group of atoms deviates significantly from planarity

Dihedral angles formed by LSQ-planes Plane - plane angle (s.u.) angle (s.u.) 1 2 6.42 (0.05) 173.58 (0.05) 1 3 4.32 (0.04) 175.68 (0.04) 2 3 3.71 (0.04) 176.29 (0.04)

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
C140.88287 (10)0.4633 (2)1.05680 (9)0.0574 (4)
C60.64520 (10)0.3453 (2)0.77842 (10)0.0564 (4)
C90.81499 (11)0.5933 (3)0.99406 (10)0.0595 (4)
C80.77912 (11)0.5429 (3)0.89464 (10)0.0647 (4)
H8A0.83310.47490.87250.078*
H8B0.76090.67950.86160.078*
C110.80051 (13)0.8395 (3)1.11760 (13)0.0777 (5)
H110.77300.96571.13720.093*
C120.86674 (12)0.7103 (3)1.17802 (12)0.0769 (5)
H120.88390.74801.23900.092*
C150.93168 (10)0.2624 (3)1.03045 (9)0.0586 (4)
C130.90730 (11)0.5258 (3)1.14784 (10)0.0683 (5)
H130.95220.43991.18900.082*
C70.68865 (11)0.3877 (3)0.87735 (10)0.0654 (4)
H7A0.70860.24780.90730.078*
H7B0.63710.45120.90410.078*
C10.67256 (13)0.1641 (3)0.73429 (12)0.0731 (5)
H10.72030.06670.76610.088*
C50.57554 (11)0.4885 (3)0.72789 (10)0.0665 (5)
H50.55680.61430.75510.080*
C100.77547 (13)0.7795 (3)1.02767 (12)0.0733 (5)
H100.73020.86700.98750.088*
C40.53347 (13)0.4477 (3)0.63793 (11)0.0778 (5)
H40.48620.54510.60540.093*
C20.63094 (14)0.1239 (3)0.64441 (12)0.0848 (6)
H20.65060.00040.61630.102*
C30.56070 (14)0.2652 (3)0.59623 (11)0.0811 (5)
H30.53180.23740.53570.097*
O10.90958 (8)0.17997 (19)0.95384 (7)0.0733 (4)
O21.00108 (8)0.1750 (2)1.09457 (7)0.0746 (4)
H2A1.0320 (17)0.036 (4)1.0726 (14)0.136 (8)*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
C140.0477 (8)0.0686 (9)0.0546 (9)0.0103 (7)0.0087 (7)0.0033 (7)
C60.0495 (8)0.0618 (9)0.0564 (9)0.0007 (7)0.0090 (7)0.0096 (7)
C90.0572 (8)0.0618 (10)0.0585 (9)0.0140 (7)0.0109 (7)0.0067 (7)
C80.0648 (9)0.0660 (10)0.0605 (9)0.0065 (7)0.0088 (7)0.0172 (7)
C110.0771 (11)0.0715 (11)0.0848 (13)0.0116 (9)0.0189 (10)0.0116 (9)
C120.0642 (10)0.0952 (13)0.0691 (11)0.0142 (9)0.0107 (8)0.0173 (10)
C150.0455 (8)0.0776 (10)0.0506 (9)0.0110 (7)0.0066 (7)0.0062 (8)
C130.0530 (9)0.0902 (12)0.0584 (10)0.0050 (8)0.0057 (7)0.0026 (8)
C70.0591 (9)0.0769 (10)0.0583 (9)0.0074 (8)0.0093 (7)0.0128 (7)
C10.0725 (10)0.0710 (11)0.0744 (11)0.0192 (8)0.0140 (8)0.0115 (9)
C50.0675 (10)0.0656 (10)0.0643 (10)0.0116 (7)0.0102 (8)0.0019 (8)
C100.0726 (11)0.0635 (11)0.0801 (12)0.0060 (8)0.0095 (9)0.0086 (9)
C40.0739 (11)0.0890 (13)0.0644 (11)0.0168 (9)0.0030 (8)0.0172 (9)
C20.1029 (14)0.0790 (12)0.0771 (13)0.0132 (10)0.0299 (11)0.0087 (10)
C30.0892 (13)0.0975 (14)0.0545 (10)0.0009 (11)0.0117 (9)0.0008 (9)
O10.0681 (7)0.0900 (9)0.0567 (7)0.0075 (6)0.0036 (5)0.0040 (6)
O20.0635 (7)0.0918 (9)0.0611 (7)0.0089 (6)0.0014 (5)0.0003 (6)
Geometric parameters (Å, º) top
C14—C131.398 (2)C15—O11.2380 (17)
C14—C91.410 (2)C15—O21.3076 (17)
C14—C151.486 (2)C13—H130.9300
C6—C11.381 (2)C7—H7A0.9700
C6—C51.384 (2)C7—H7B0.9700
C6—C71.506 (2)C1—C21.375 (2)
C9—C101.396 (2)C1—H10.9300
C9—C81.508 (2)C5—C41.378 (2)
C8—C71.529 (2)C5—H50.9300
C8—H8A0.9700C10—H100.9300
C8—H8B0.9700C4—C31.366 (2)
C11—C121.377 (2)C4—H40.9300
C11—C101.378 (2)C2—C31.368 (2)
C11—H110.9300C2—H20.9300
C12—C131.372 (2)C3—H30.9300
C12—H120.9300O2—H2A1.03 (2)
C13—C14—C9119.33 (15)C14—C13—H13119.1
C13—C14—C15117.79 (13)C6—C7—C8113.36 (12)
C9—C14—C15122.88 (13)C6—C7—H7A108.9
C1—C6—C5117.22 (15)C8—C7—H7A108.9
C1—C6—C7121.97 (14)C6—C7—H7B108.9
C5—C6—C7120.82 (14)C8—C7—H7B108.9
C10—C9—C14117.04 (14)H7A—C7—H7B107.7
C10—C9—C8117.63 (14)C2—C1—C6121.63 (15)
C14—C9—C8125.29 (15)C2—C1—H1119.2
C9—C8—C7111.27 (12)C6—C1—H1119.2
C9—C8—H8A109.4C4—C5—C6121.13 (15)
C7—C8—H8A109.4C4—C5—H5119.4
C9—C8—H8B109.4C6—C5—H5119.4
C7—C8—H8B109.4C11—C10—C9123.01 (17)
H8A—C8—H8B108.0C11—C10—H10118.5
C12—C11—C10119.19 (18)C9—C10—H10118.5
C12—C11—H11120.4C3—C4—C5120.47 (15)
C10—C11—H11120.4C3—C4—H4119.8
C13—C12—C11119.69 (16)C5—C4—H4119.8
C13—C12—H12120.2C3—C2—C1120.15 (16)
C11—C12—H12120.2C3—C2—H2119.9
O1—C15—O2121.14 (16)C1—C2—H2119.9
O1—C15—C14123.63 (13)C4—C3—C2119.38 (16)
O2—C15—C14115.23 (13)C4—C3—H3120.3
C12—C13—C14121.75 (15)C2—C3—H3120.3
C12—C13—H13119.1C15—O2—H2A111.8 (12)
C13—C14—C9—C100.2 (2)C1—C6—C7—C894.57 (18)
C15—C14—C9—C10179.22 (12)C5—C6—C7—C885.45 (18)
C13—C14—C9—C8177.93 (13)C9—C8—C7—C6175.78 (13)
C15—C14—C9—C83.1 (2)C5—C6—C1—C21.4 (2)
C10—C9—C8—C791.62 (17)C7—C6—C1—C2178.57 (15)
C14—C9—C8—C786.09 (18)C1—C6—C5—C41.7 (2)
C10—C11—C12—C130.6 (3)C7—C6—C5—C4178.26 (13)
C13—C14—C15—O1173.39 (13)C12—C11—C10—C90.7 (3)
C9—C14—C15—O17.6 (2)C14—C9—C10—C110.5 (2)
C13—C14—C15—O26.49 (19)C8—C9—C10—C11178.36 (14)
C9—C14—C15—O2172.54 (12)C6—C5—C4—C30.8 (3)
C11—C12—C13—C140.4 (2)C6—C1—C2—C30.1 (3)
C9—C14—C13—C120.2 (2)C5—C4—C3—C20.6 (3)
C15—C14—C13—C12179.23 (14)C1—C2—C3—C40.9 (3)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
O2—H2A···O1i1.03 (2)1.63 (2)2.657 (2)174 (2)
Symmetry code: (i) x+2, y, z+2.
 

Subscribe to Acta Crystallographica Section E: Crystallographic Communications

The full text of this article is available to subscribers to the journal.

If you have already registered and are using a computer listed in your registration details, please email support@iucr.org for assistance.

Buy online

You may purchase this article in PDF and/or HTML formats. For purchasers in the European Community who do not have a VAT number, VAT will be added at the local rate. Payments to the IUCr are handled by WorldPay, who will accept payment by credit card in several currencies. To purchase the article, please complete the form below (fields marked * are required), and then click on `Continue'.
E-mail address* 
Repeat e-mail address* 
(for error checking) 

Format*   PDF (US $40)
   HTML (US $40)
   PDF+HTML (US $50)
In order for VAT to be shown for your country javascript needs to be enabled.

VAT number 
(non-UK EC countries only) 
Country* 
 

Terms and conditions of use
Contact us

Follow Acta Cryst. E
Sign up for e-alerts
Follow Acta Cryst. on Twitter
Follow us on facebook
Sign up for RSS feeds