3,5-Bis(benz-yloxy)benzoic acid.

In the title compound, C(21)H(18)O(4), the outer benzyl rings are disordered over two resolved positions in a 0.50 ratio. The O-CH(2) groups form dihedral angles of 4.1 (2) and 10.9 (4)° with the central benzene ring, adopting a syn-anti conformation with respect to this ring. In the crystal, the mol-ecules are linked by O-H⋯O hydrogen bonds and weak C-H⋯O inter-actions, forming chains along [010].

Related literature

For properties of dendrimer chemistry, see: Fréchet (2002 ▶). For the diverse applications of 3,5-bis­(benz­yloxy)benzoic acid and its benzoate derivatives, see: Sivakumar et al. (2010 ▶); Remya et al. (2008 ▶); Hawker & Fréchet (1992 ▶). For magnetic and luminiscent properties of lanthanide benzoates, see: Busskamp et al. (2007 ▶). For the conformation of O—CH2 groups, see: Xiao et al. (2007 ▶). For related structures, see: Gainsford et al. (2009 ▶); Zhu et al. (2009 ▶). For graph-set motifs, see: Etter (1990 ▶). For hydrogen bonding, see: Nardelli (1995 ▶); Desiraju & Steiner (1999 ▶).

Experimental

Crystal data

C21H18O4

M = 334.37

Triclinic,

a = 5.2801 (2) Å

b = 11.6830 (5) Å

c = 14.4803 (7) Å

α = 83.303 (2)°

β = 80.775 (2)°

γ = 79.031 (1)°

V = 862.17 (6) Å3

Z = 2

Mo Kα radiation

μ = 0.09 mm−1

T = 295 K

0.43 × 0.11 × 0.10 mm

Data collection

Nonius KappaCCD diffractometer

5626 measured reflections

3084 independent reflections

1801 reflections with I > 2σ(I)

R int = 0.036

Refinement

R[F 2 > 2σ(F 2)] = 0.053

wR(F 2) = 0.163

S = 1.03

3084 reflections

316 parameters

H-atom parameters constrained

Δρmax = 0.15 e Å−3

Δρmin = −0.15 e Å−3

Data collection: COLLECT (Nonius, 2000 ▶); cell refinement: SCALEPACK (Otwinowski & Minor, 1997 ▶); data reduction: DENZO (Otwinowski & Minor, 1997 ▶) and SCALEPACK; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: ORTEP-3 for Windows (Farrugia, 1997 ▶) and Mercury (Macrae et al., 2006 ▶); software used to prepare material for publication: WinGX (Farrugia, 1999 ▶).

Click here for additional data file.

Crystal structure: contains datablock(s) I, global. DOI: 10.1107/S1600536812043796/hg5257sup1.cif

Click here for additional data file.

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536812043796/hg5257Isup2.hkl

Click here for additional data file.

Supplementary material file. DOI: 10.1107/S1600536812043796/hg5257Isup3.cml

Additional supplementary materials: crystallographic information; 3D view; checkCIF report

C21H18O4	Z = 2
Mr = 334.37	F(000) = 352
Triclinic, P1	Dx = 1.288 Mg m−3
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 5.2801 (2) Å	Cell parameters from 3147 reflections
b = 11.6830 (5) Å	θ = 2.9–26.4°
c = 14.4803 (7) Å	µ = 0.09 mm−1
α = 83.303 (2)°	T = 295 K
β = 80.775 (2)°	Block, colourless
γ = 79.031 (1)°	0.43 × 0.11 × 0.10 mm
V = 862.17 (6) Å3

Nonius KappaCCD diffractometer	1801 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	Rint = 0.036
Graphite monochromator	θmax = 25.2°, θmin = 3.5°
CCD rotation images, thick slices scans	h = −6→6
5626 measured reflections	k = −14→14
3084 independent reflections	l = −17→17

Refinement on F2	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.053	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.163	H-atom parameters constrained
S = 1.03	w = 1/[σ2(Fo2) + (0.094P)2 + 0.0032P] where P = (Fo2 + 2Fc2)/3
3084 reflections	(Δ/σ)max < 0.001
316 parameters	Δρmax = 0.15 e Å−3
0 restraints	Δρmin = −0.15 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.

	x	y	z	Uiso*/Ueq	Occ. (<1)
C1	0.2556 (3)	0.46372 (17)	0.58387 (13)	0.0623 (5)
C2	0.4505 (3)	0.43437 (15)	0.65014 (12)	0.0597 (5)
C3	0.4690 (3)	0.51344 (17)	0.71085 (12)	0.0644 (5)
H3	0.3589	0.5858	0.7109	0.077*
C4	0.6534 (3)	0.48473 (16)	0.77226 (12)	0.0639 (5)
C5	0.8181 (4)	0.37791 (17)	0.77144 (13)	0.0673 (5)
H5	0.9413	0.3585	0.8125	0.081*
C6	0.7989 (4)	0.29977 (17)	0.70920 (14)	0.0690 (5)
C7	0.6163 (3)	0.32636 (17)	0.64802 (13)	0.0690 (5)
H7	0.6042	0.2734	0.6064	0.083*
C8	0.8524 (4)	0.55033 (19)	0.88979 (15)	0.0773 (6)
H8A	1.0236	0.5321	0.8534	0.093*
H8B	0.8282	0.4854	0.9366	0.093*
C9	0.8300 (5)	0.65976 (19)	0.93627 (17)	0.0705 (6)	0.50
C11	0.592 (6)	0.802 (3)	1.0445 (16)	0.132 (8)	0.50
H11	0.4429	0.8290	1.0849	0.159*	0.50
C10	0.626 (5)	0.699 (2)	0.9975 (15)	0.112 (6)	0.50
H10	0.4933	0.6553	1.0109	0.134*	0.50
C12	0.798 (6)	0.854 (3)	1.0238 (16)	0.128 (9)	0.50
H12	0.7988	0.9192	1.0546	0.153*	0.50
C13	1.003 (4)	0.8186 (14)	0.9621 (15)	0.109 (4)	0.50
H13	1.1409	0.8600	0.9478	0.131*	0.50
C14	1.007 (3)	0.7216 (16)	0.9208 (10)	0.089 (4)	0.50
H14	1.1510	0.6978	0.8771	0.107*	0.50
C15	1.0002 (5)	0.1234 (2)	0.64080 (18)	0.0965 (8)
H15A	1.0431	0.1663	0.5806	0.116*
H15B	0.8372	0.0966	0.6407	0.116*
O1	0.2389 (2)	0.39389 (12)	0.52819 (9)	0.0771 (4)
O2	0.1076 (2)	0.56551 (11)	0.58910 (9)	0.0786 (5)
H2	0.0056	0.5746	0.5506	0.118*
O3	0.6562 (3)	0.56890 (12)	0.82994 (9)	0.0821 (5)
O4	0.9731 (3)	0.19714 (13)	0.71375 (11)	0.0918 (5)
C16	1.2137 (4)	0.01969 (19)	0.65555 (17)	0.0819 (6)	0.50
C17	1.311 (3)	−0.0007 (14)	0.7341 (13)	0.123 (6)	0.50
H17	1.2647	0.0503	0.7812	0.148*	0.50
C18	1.498 (2)	−0.1088 (13)	0.7431 (10)	0.118 (4)	0.50
H18	1.5568	−0.1319	0.8008	0.141*	0.50
C19	1.592 (4)	−0.1779 (19)	0.672 (2)	0.107 (7)	0.50
H19	1.7133	−0.2461	0.6796	0.128*	0.50
C20	1.506 (2)	−0.1445 (10)	0.5925 (11)	0.119 (4)	0.50
H20	1.5708	−0.1903	0.5427	0.143*	0.50
C21	1.3231 (14)	−0.0455 (7)	0.5771 (6)	0.102 (2)	0.50
H21	1.2735	−0.0222	0.5180	0.123*	0.50
C21A	1.388 (3)	0.0108 (12)	0.7188 (12)	0.087 (4)	0.50
H21A	1.3649	0.0714	0.7574	0.105*	0.50
C17A	1.2212 (16)	−0.0818 (6)	0.6129 (5)	0.091 (2)	0.50
H17A	1.0879	−0.0863	0.5792	0.110*	0.50
C18A	1.420 (2)	−0.1752 (10)	0.6191 (9)	0.104 (3)	0.50
H18A	1.4344	−0.2395	0.5851	0.124*	0.50
C19A	1.604 (4)	−0.170 (2)	0.680 (2)	0.116 (9)	0.50
H19A	1.7397	−0.2329	0.6857	0.139*	0.50
C20A	1.588 (3)	−0.0765 (13)	0.7298 (13)	0.109 (4)	0.50
H20A	1.7085	−0.0737	0.7693	0.131*	0.50
C11A	0.945 (5)	0.8536 (15)	0.9366 (15)	0.122 (5)	0.50
H11A	1.0322	0.9136	0.9086	0.146*	0.50
C9A	0.8300 (5)	0.65976 (19)	0.93627 (17)	0.0705 (6)	0.50
C10A	0.986 (4)	0.7480 (16)	0.8932 (12)	0.101 (4)	0.50
H10A	1.1073	0.7352	0.8397	0.121*	0.50
C12A	0.777 (5)	0.870 (2)	1.021 (2)	0.118 (8)	0.50
H12A	0.7512	0.9388	1.0496	0.141*	0.50
C14A	0.663 (4)	0.678 (2)	1.0200 (13)	0.081 (3)	0.50
H14A	0.5643	0.6216	1.0477	0.097*	0.50
C13A	0.645 (4)	0.776 (2)	1.0596 (13)	0.096 (5)	0.50
H13A	0.5398	0.7840	1.1172	0.115*	0.50
C16A	1.2137 (4)	0.01969 (19)	0.65555 (17)	0.0819 (6)	0.50

	U11	U22	U33	U12	U13	U23
C1	0.0606 (10)	0.0610 (12)	0.0628 (11)	−0.0002 (9)	−0.0110 (9)	−0.0101 (9)
C2	0.0577 (10)	0.0599 (12)	0.0602 (11)	−0.0032 (8)	−0.0116 (8)	−0.0069 (9)
C3	0.0648 (11)	0.0612 (12)	0.0641 (11)	0.0030 (8)	−0.0142 (9)	−0.0097 (9)
C4	0.0703 (11)	0.0595 (12)	0.0620 (11)	−0.0017 (9)	−0.0167 (9)	−0.0125 (9)
C5	0.0692 (11)	0.0666 (13)	0.0666 (12)	0.0001 (9)	−0.0224 (9)	−0.0100 (10)
C6	0.0713 (11)	0.0596 (12)	0.0744 (12)	0.0063 (9)	−0.0215 (10)	−0.0127 (10)
C7	0.0713 (11)	0.0648 (13)	0.0712 (12)	0.0012 (10)	−0.0203 (9)	−0.0145 (9)
C8	0.0778 (12)	0.0754 (14)	0.0830 (14)	−0.0039 (10)	−0.0320 (11)	−0.0114 (11)
C9	0.0755 (13)	0.0689 (13)	0.0719 (14)	−0.0086 (12)	−0.0259 (12)	−0.0111 (11)
C11	0.158 (16)	0.098 (11)	0.134 (13)	−0.007 (10)	0.007 (10)	−0.043 (10)
C10	0.144 (13)	0.095 (10)	0.103 (12)	−0.048 (9)	−0.001 (8)	−0.017 (8)
C12	0.20 (2)	0.100 (12)	0.089 (10)	−0.025 (10)	−0.011 (10)	−0.054 (8)
C13	0.111 (6)	0.079 (8)	0.146 (14)	−0.022 (6)	−0.025 (7)	−0.022 (7)
C14	0.090 (4)	0.078 (7)	0.096 (10)	−0.009 (4)	−0.006 (6)	−0.018 (6)
C15	0.1051 (16)	0.0757 (16)	0.1102 (18)	0.0201 (12)	−0.0423 (14)	−0.0365 (13)
O1	0.0803 (9)	0.0747 (9)	0.0783 (9)	0.0080 (7)	−0.0301 (7)	−0.0240 (7)
O2	0.0789 (8)	0.0692 (9)	0.0882 (10)	0.0108 (7)	−0.0338 (7)	−0.0184 (7)
O3	0.0962 (10)	0.0701 (9)	0.0839 (9)	0.0106 (7)	−0.0419 (8)	−0.0244 (7)
O4	0.1028 (10)	0.0712 (10)	0.1016 (11)	0.0268 (8)	−0.0480 (8)	−0.0317 (8)
C16	0.0851 (14)	0.0636 (14)	0.0955 (17)	0.0050 (11)	−0.0223 (13)	−0.0177 (12)
C17	0.118 (12)	0.134 (9)	0.086 (5)	0.055 (7)	−0.017 (7)	0.000 (5)
C18	0.134 (10)	0.096 (9)	0.104 (5)	0.034 (7)	−0.035 (7)	0.007 (6)
C19	0.131 (12)	0.051 (9)	0.136 (13)	0.002 (7)	−0.035 (11)	−0.007 (8)
C20	0.116 (7)	0.079 (7)	0.158 (11)	0.010 (5)	−0.011 (6)	−0.051 (6)
C21	0.107 (5)	0.080 (5)	0.120 (6)	0.019 (4)	−0.032 (4)	−0.041 (4)
C21A	0.082 (6)	0.072 (4)	0.107 (9)	0.013 (4)	−0.023 (5)	−0.037 (5)
C17A	0.112 (5)	0.066 (4)	0.096 (5)	−0.002 (3)	−0.026 (4)	−0.011 (3)
C18A	0.137 (9)	0.054 (5)	0.115 (6)	−0.002 (5)	−0.022 (6)	−0.007 (4)
C19A	0.090 (9)	0.087 (15)	0.138 (14)	0.036 (8)	0.012 (11)	0.002 (9)
C20A	0.087 (6)	0.082 (7)	0.158 (9)	−0.002 (5)	−0.038 (6)	−0.007 (6)
C11A	0.173 (15)	0.083 (10)	0.123 (10)	−0.058 (9)	−0.027 (9)	−0.006 (7)
C9A	0.0755 (13)	0.0689 (13)	0.0719 (14)	−0.0086 (12)	−0.0259 (12)	−0.0111 (11)
C10A	0.143 (9)	0.094 (9)	0.076 (7)	−0.058 (6)	−0.004 (5)	−0.011 (6)
C12A	0.127 (10)	0.082 (8)	0.162 (19)	−0.026 (7)	−0.043 (11)	−0.042 (8)
C14A	0.098 (5)	0.088 (9)	0.059 (6)	−0.027 (5)	−0.002 (4)	−0.017 (5)
C13A	0.109 (7)	0.112 (15)	0.069 (4)	−0.025 (8)	0.001 (5)	−0.027 (6)
C16A	0.0851 (14)	0.0636 (14)	0.0955 (17)	0.0050 (11)	−0.0223 (13)	−0.0177 (12)

C1—O1	1.236 (2)	C15—H15B	0.9700
C1—O2	1.296 (2)	O2—H2	0.8200
C1—C2	1.484 (2)	C16—C17	1.302 (18)
C2—C3	1.374 (2)	C16—C21	1.424 (8)
C2—C7	1.393 (2)	C17—C18	1.45 (2)
C3—C4	1.391 (2)	C17—H17	0.9300
C3—H3	0.9300	C18—C19	1.36 (3)
C4—O3	1.366 (2)	C18—H18	0.9300
C4—C5	1.379 (3)	C19—C20	1.30 (4)
C5—C6	1.383 (3)	C19—H19	0.9300
C5—H5	0.9300	C20—C21	1.379 (14)
C6—O4	1.367 (2)	C20—H20	0.9300
C6—C7	1.381 (3)	C21—H21	0.9300
C7—H7	0.9300	C21A—C20A	1.33 (2)
C8—O3	1.425 (2)	C21A—H21A	0.9300
C8—C9	1.490 (3)	C17A—C18A	1.369 (14)
C8—H8A	0.9700	C17A—H17A	0.9300
C8—H8B	0.9700	C18A—C19A	1.42 (4)
C9—C14	1.26 (2)	C18A—H18A	0.9300
C9—C10	1.33 (3)	C19A—C20A	1.36 (3)
C11—C12	1.32 (5)	C19A—H19A	0.9300
C11—C10	1.41 (4)	C20A—H20A	0.9300
C11—H11	0.9300	C11A—C12A	1.40 (3)
C10—H10	0.9300	C11A—C10A	1.41 (3)
C12—C13	1.32 (3)	C11A—H11A	0.9300
C12—H12	0.9300	C10A—H10A	0.9300
C13—C14	1.34 (3)	C12A—C13A	1.42 (4)
C13—H13	0.9300	C12A—H12A	0.9300
C14—H14	0.9300	C14A—C13A	1.32 (3)
C15—O4	1.413 (3)	C14A—H14A	0.9300
C15—C16	1.510 (3)	C13A—H13A	0.9300
C15—H15A	0.9700
O1—C1—O2	123.33 (16)	C16—C15—H15A	109.8
O1—C1—C2	121.00 (16)	O4—C15—H15B	109.8
O2—C1—C2	115.67 (16)	C16—C15—H15B	109.8
C3—C2—C7	121.05 (17)	H15A—C15—H15B	108.3
C3—C2—C1	120.35 (16)	C1—O2—H2	109.5
C7—C2—C1	118.59 (16)	C4—O3—C8	118.81 (14)
C2—C3—C4	119.62 (17)	C6—O4—C15	117.70 (15)
C2—C3—H3	120.2	C17—C16—C21	121.6 (8)
C4—C3—H3	120.2	C17—C16—C15	120.5 (8)
O3—C4—C5	124.69 (16)	C21—C16—C15	117.4 (4)
O3—C4—C3	115.23 (16)	C16—C17—C18	115.3 (14)
C5—C4—C3	120.07 (17)	C16—C17—H17	122.4
C4—C5—C6	119.60 (17)	C18—C17—H17	122.4
C4—C5—H5	120.2	C19—C18—C17	123.6 (17)
C6—C5—H5	120.2	C19—C18—H18	118.2
O4—C6—C7	124.09 (17)	C17—C18—H18	118.2
O4—C6—C5	114.69 (16)	C20—C19—C18	117.0 (17)
C7—C6—C5	121.21 (17)	C20—C19—H19	121.5
C6—C7—C2	118.43 (17)	C18—C19—H19	121.5
C6—C7—H7	120.8	C19—C20—C21	124.2 (14)
C2—C7—H7	120.8	C19—C20—H20	117.9
O3—C8—C9	107.77 (15)	C21—C20—H20	117.9
O3—C8—H8A	110.2	C20—C21—C16	117.1 (9)
C9—C8—H8A	110.2	C20—C21—H21	121.4
O3—C8—H8B	110.2	C16—C21—H21	121.4
C9—C8—H8B	110.2	C20A—C21A—H21A	116.9
H8A—C8—H8B	108.5	C18A—C17A—H17A	119.2
C14—C9—C10	114.7 (15)	C17A—C18A—C19A	117.3 (13)
C14—C9—C8	122.2 (8)	C17A—C18A—H18A	121.3
C10—C9—C8	123.1 (13)	C19A—C18A—H18A	121.3
C12—C11—C10	112 (3)	C20A—C19A—C18A	122.3 (15)
C12—C11—H11	124.2	C20A—C19A—H19A	118.8
C10—C11—H11	124.2	C18A—C19A—H19A	118.8
C9—C10—C11	126 (3)	C21A—C20A—C19A	116.2 (16)
C9—C10—H10	116.9	C21A—C20A—H20A	121.9
C11—C10—H10	116.9	C19A—C20A—H20A	121.9
C13—C12—C11	124 (3)	C12A—C11A—C10A	121.5 (19)
C13—C12—H12	117.9	C12A—C11A—H11A	119.3
C11—C12—H12	117.9	C10A—C11A—H11A	119.3
C12—C13—C14	118 (2)	C11A—C10A—H10A	121.4
C12—C13—H13	121.1	C11A—C12A—C13A	117 (2)
C14—C13—H13	121.1	C11A—C12A—H12A	121.6
C9—C14—C13	125.4 (14)	C13A—C12A—H12A	121.6
C9—C14—H14	117.3	C13A—C14A—H14A	120.4
C13—C14—H14	117.3	C14A—C13A—C12A	125 (2)
O4—C15—C16	109.24 (18)	C14A—C13A—H13A	117.6
O4—C15—H15A	109.8	C12A—C13A—H13A	117.6
O1—C1—C2—C3	179.21 (16)	C10—C9—C14—C13	1.5 (18)
O2—C1—C2—C3	−1.0 (2)	C8—C9—C14—C13	−177.8 (11)
O1—C1—C2—C7	0.4 (3)	C12—C13—C14—C9	0 (3)
O2—C1—C2—C7	−179.85 (16)	C5—C4—O3—C8	4.4 (3)
C7—C2—C3—C4	−1.0 (3)	C3—C4—O3—C8	−175.13 (16)
C1—C2—C3—C4	−179.76 (15)	C9—C8—O3—C4	173.58 (17)
C2—C3—C4—O3	−179.84 (15)	C7—C6—O4—C15	12.0 (3)
C2—C3—C4—C5	0.6 (3)	C5—C6—O4—C15	−167.82 (19)
O3—C4—C5—C6	−179.43 (16)	C16—C15—O4—C6	176.14 (18)
C3—C4—C5—C6	0.1 (3)	O4—C15—C16—C17	11.0 (9)
C4—C5—C6—O4	179.37 (17)	O4—C15—C16—C21	−161.8 (4)
C4—C5—C6—C7	−0.4 (3)	C21—C16—C17—C18	−12.9 (17)
O4—C6—C7—C2	−179.70 (18)	C15—C16—C17—C18	174.6 (9)
C5—C6—C7—C2	0.1 (3)	C16—C17—C18—C19	8 (2)
C3—C2—C7—C6	0.6 (3)	C17—C18—C19—C20	−1 (3)
C1—C2—C7—C6	179.44 (16)	C18—C19—C20—C21	−1 (3)
O3—C8—C9—C14	−114.4 (7)	C19—C20—C21—C16	−3.7 (18)
O3—C8—C9—C10	66.4 (9)	C17—C16—C21—C20	11.5 (13)
C14—C9—C10—C11	1 (2)	C15—C16—C21—C20	−175.8 (6)
C8—C9—C10—C11	179.8 (15)	C17A—C18A—C19A—C20A	−1 (3)
C12—C11—C10—C9	−3 (3)	C18A—C19A—C20A—C21A	0 (3)
C10—C11—C12—C13	4 (4)	C10A—C11A—C12A—C13A	−1 (3)
C11—C12—C13—C14	−3 (4)	C11A—C12A—C13A—C14A	−3 (4)

D—H···A	D—H	H···A	D···A	D—H···A
O2—H2···O1i	0.82	1.82	2.6333 (18)	175
C20—H20···O1ii	0.93	2.66	3.507 (13)	153

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O2—H2⋯O1i	0.82	1.82	2.6333 (18)	175
C20—H20⋯O1ii	0.93	2.66	3.507 (13)	153

Symmetry codes: (i) ; (ii) .