Inter­molecularly associated carboxylic acid dimers in the supramolecular assembly of 2-(2-phenyl­ethyl)benzoic acid

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.

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

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

Crystal data

C15H14O2	F(000) = 480
Mr = 226.26	Dx = 1.227 Mg m^−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 1036 reflections
a = 13.7005 (2) Å	θ = 5–35°
b = 6.0509 (1) Å	µ = 0.08 mm^−1
c = 15.1789 (1) Å	T = 293 K
β = 103.155 (1)°	Block, colorless
V = 1225.32 (3) Å^3	0.14 × 0.12 × 0.08 mm
Z = 4

Data collection

Siemens SMART CCD area-detector diffractometer	1421 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	Rint = 0.024
Graphite monochromator	θmax = 23.3°, θmin = 1.5°
ω scans	h = −15→14
4864 measured reflections	k = −6→6
1761 independent reflections	l = −16→14

Refinement

Refinement on F^2	Secondary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F^2 > 2σ(F^2)] = 0.038	H atoms treated by a mixture of independent and constrained refinement
wR(F^2) = 0.114	w = 1/[σ^2(Fo^2) + (0.0746P)^2] where P = (Fo^2 + 2Fc^2)/3
S = 1.08	(Δ/σ)max = 0.001
1761 reflections	Δρmax = 0.18 e Å^−3
159 parameters	Δρmin = −0.13 e Å^−3
0 restraints	Extinction correction: SHELXL97, Fc^*=kFc[1+0.001xFc^2λ^3/sin(2θ)]^-1/4
Primary atom site location: structure-invariant direct methods	Extinction coefficient: 0.030 (4)

Special details

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 (Ų)

	x	y	z	Uiso*/Ueq
C14	0.88287 (10)	0.4633 (2)	1.05680 (9)	0.0574 (4)
C6	0.64520 (10)	0.3453 (2)	0.77842 (10)	0.0564 (4)
C9	0.81499 (11)	0.5933 (3)	0.99406 (10)	0.0595 (4)
C8	0.77912 (11)	0.5429 (3)	0.89464 (10)	0.0647 (4)
H8A	0.8331	0.4749	0.8725	0.078*
H8B	0.7609	0.6795	0.8616	0.078*
C11	0.80051 (13)	0.8395 (3)	1.11760 (13)	0.0777 (5)
H11	0.7730	0.9657	1.1372	0.093*
C12	0.86674 (12)	0.7103 (3)	1.17802 (12)	0.0769 (5)
H12	0.8839	0.7480	1.2390	0.092*
C15	0.93168 (10)	0.2624 (3)	1.03045 (9)	0.0586 (4)
C13	0.90730 (11)	0.5258 (3)	1.14784 (10)	0.0683 (5)
H13	0.9522	0.4399	1.1890	0.082*
C7	0.68865 (11)	0.3877 (3)	0.87735 (10)	0.0654 (4)
H7A	0.7086	0.2478	0.9073	0.078*
H7B	0.6371	0.4512	0.9041	0.078*
C1	0.67256 (13)	0.1641 (3)	0.73429 (12)	0.0731 (5)
H1	0.7203	0.0667	0.7661	0.088*
C5	0.57554 (11)	0.4885 (3)	0.72789 (10)	0.0665 (5)
H5	0.5568	0.6143	0.7551	0.080*
C10	0.77547 (13)	0.7795 (3)	1.02767 (12)	0.0733 (5)
H10	0.7302	0.8670	0.9875	0.088*
C4	0.53347 (13)	0.4477 (3)	0.63793 (11)	0.0778 (5)
H4	0.4862	0.5451	0.6054	0.093*
C2	0.63094 (14)	0.1239 (3)	0.64441 (12)	0.0848 (6)
H2	0.6506	0.0004	0.6163	0.102*
C3	0.56070 (14)	0.2652 (3)	0.59623 (11)	0.0811 (5)
H3	0.5318	0.2374	0.5357	0.097*
O1	0.90958 (8)	0.17997 (19)	0.95384 (7)	0.0733 (4)
O2	1.00108 (8)	0.1750 (2)	1.09457 (7)	0.0746 (4)
H2A	1.0320 (17)	0.036 (4)	1.0726 (14)	0.136 (8)*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
C14	0.0477 (8)	0.0686 (9)	0.0546 (9)	−0.0103 (7)	0.0087 (7)	0.0033 (7)
C6	0.0495 (8)	0.0618 (9)	0.0564 (9)	−0.0007 (7)	0.0090 (7)	0.0096 (7)
C9	0.0572 (8)	0.0618 (10)	0.0585 (9)	−0.0140 (7)	0.0109 (7)	0.0067 (7)
C8	0.0648 (9)	0.0660 (10)	0.0605 (9)	−0.0065 (7)	0.0088 (7)	0.0172 (7)
C11	0.0771 (11)	0.0715 (11)	0.0848 (13)	−0.0116 (9)	0.0189 (10)	−0.0116 (9)
C12	0.0642 (10)	0.0952 (13)	0.0691 (11)	−0.0142 (9)	0.0107 (8)	−0.0173 (10)
C15	0.0455 (8)	0.0776 (10)	0.0506 (9)	−0.0110 (7)	0.0066 (7)	0.0062 (8)
C13	0.0530 (9)	0.0902 (12)	0.0584 (10)	−0.0050 (8)	0.0057 (7)	−0.0026 (8)
C7	0.0591 (9)	0.0769 (10)	0.0583 (9)	−0.0074 (8)	0.0093 (7)	0.0128 (7)
C1	0.0725 (10)	0.0710 (11)	0.0744 (11)	0.0192 (8)	0.0140 (8)	0.0115 (9)
C5	0.0675 (10)	0.0656 (10)	0.0643 (10)	0.0116 (7)	0.0102 (8)	0.0019 (8)
C10	0.0726 (11)	0.0635 (11)	0.0801 (12)	−0.0060 (8)	0.0095 (9)	0.0086 (9)
C4	0.0739 (11)	0.0890 (13)	0.0644 (11)	0.0168 (9)	0.0030 (8)	0.0172 (9)
C2	0.1029 (14)	0.0790 (12)	0.0771 (13)	0.0132 (10)	0.0299 (11)	−0.0087 (10)
C3	0.0892 (13)	0.0975 (14)	0.0545 (10)	−0.0009 (11)	0.0117 (9)	−0.0008 (9)
O1	0.0681 (7)	0.0900 (9)	0.0567 (7)	0.0075 (6)	0.0036 (5)	−0.0040 (6)
O2	0.0635 (7)	0.0918 (9)	0.0611 (7)	0.0089 (6)	−0.0014 (5)	0.0003 (6)

Geometric parameters (Å, º)

C14—C13	1.398 (2)	C15—O1	1.2380 (17)
C14—C9	1.410 (2)	C15—O2	1.3076 (17)
C14—C15	1.486 (2)	C13—H13	0.9300
C6—C1	1.381 (2)	C7—H7A	0.9700
C6—C5	1.384 (2)	C7—H7B	0.9700
C6—C7	1.506 (2)	C1—C2	1.375 (2)
C9—C10	1.396 (2)	C1—H1	0.9300
C9—C8	1.508 (2)	C5—C4	1.378 (2)
C8—C7	1.529 (2)	C5—H5	0.9300
C8—H8A	0.9700	C10—H10	0.9300
C8—H8B	0.9700	C4—C3	1.366 (2)
C11—C12	1.377 (2)	C4—H4	0.9300
C11—C10	1.378 (2)	C2—C3	1.368 (2)
C11—H11	0.9300	C2—H2	0.9300
C12—C13	1.372 (2)	C3—H3	0.9300
C12—H12	0.9300	O2—H2A	1.03 (2)
C13—C14—C9	119.33 (15)	C14—C13—H13	119.1
C13—C14—C15	117.79 (13)	C6—C7—C8	113.36 (12)
C9—C14—C15	122.88 (13)	C6—C7—H7A	108.9
C1—C6—C5	117.22 (15)	C8—C7—H7A	108.9
C1—C6—C7	121.97 (14)	C6—C7—H7B	108.9
C5—C6—C7	120.82 (14)	C8—C7—H7B	108.9
C10—C9—C14	117.04 (14)	H7A—C7—H7B	107.7
C10—C9—C8	117.63 (14)	C2—C1—C6	121.63 (15)
C14—C9—C8	125.29 (15)	C2—C1—H1	119.2
C9—C8—C7	111.27 (12)	C6—C1—H1	119.2
C9—C8—H8A	109.4	C4—C5—C6	121.13 (15)
C7—C8—H8A	109.4	C4—C5—H5	119.4
C9—C8—H8B	109.4	C6—C5—H5	119.4
C7—C8—H8B	109.4	C11—C10—C9	123.01 (17)
H8A—C8—H8B	108.0	C11—C10—H10	118.5
C12—C11—C10	119.19 (18)	C9—C10—H10	118.5
C12—C11—H11	120.4	C3—C4—C5	120.47 (15)
C10—C11—H11	120.4	C3—C4—H4	119.8
C13—C12—C11	119.69 (16)	C5—C4—H4	119.8
C13—C12—H12	120.2	C3—C2—C1	120.15 (16)
C11—C12—H12	120.2	C3—C2—H2	119.9
O1—C15—O2	121.14 (16)	C1—C2—H2	119.9
O1—C15—C14	123.63 (13)	C4—C3—C2	119.38 (16)
O2—C15—C14	115.23 (13)	C4—C3—H3	120.3
C12—C13—C14	121.75 (15)	C2—C3—H3	120.3
C12—C13—H13	119.1	C15—O2—H2A	111.8 (12)
C13—C14—C9—C10	−0.2 (2)	C1—C6—C7—C8	94.57 (18)
C15—C14—C9—C10	−179.22 (12)	C5—C6—C7—C8	−85.45 (18)
C13—C14—C9—C8	−177.93 (13)	C9—C8—C7—C6	175.78 (13)
C15—C14—C9—C8	3.1 (2)	C5—C6—C1—C2	−1.4 (2)
C10—C9—C8—C7	−91.62 (17)	C7—C6—C1—C2	178.57 (15)
C14—C9—C8—C7	86.09 (18)	C1—C6—C5—C4	1.7 (2)
C10—C11—C12—C13	0.6 (3)	C7—C6—C5—C4	−178.26 (13)
C13—C14—C15—O1	173.39 (13)	C12—C11—C10—C9	−0.7 (3)
C9—C14—C15—O1	−7.6 (2)	C14—C9—C10—C11	0.5 (2)
C13—C14—C15—O2	−6.49 (19)	C8—C9—C10—C11	178.36 (14)
C9—C14—C15—O2	172.54 (12)	C6—C5—C4—C3	−0.8 (3)
C11—C12—C13—C14	−0.4 (2)	C6—C1—C2—C3	0.1 (3)
C9—C14—C13—C12	0.2 (2)	C5—C4—C3—C2	−0.6 (3)
C15—C14—C13—C12	179.23 (14)	C1—C2—C3—C4	0.9 (3)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
O2—H2A···O1^i	1.03 (2)	1.63 (2)	2.657 (2)	174 (2)

Symmetry code: (i) −x+2, −y, −z+2.