Benzene-1,3,5-triyl tribenzoate.

The title compound, C27H18O6, commonly known as phloroglucinol tribenzoate, is a standard unit for the family of benzyl ether dendrimers. The central phloroglucinol residue is close to planar, with out-of-plane distances for the three oxygen atoms of up to 0.095 (3) Å, while the three attached benzoate groups are approximately planar. One benzoate group is twisted [C-C-O-C torsion angle = 98.2 (3)°] from the central plane, with its carbonyl O atom 2.226 (4) Å above that plane, while the other two benzoate groups are twisted in the opposite direction [C-C-O-C torsion angles = 24.7 (2) and 54.8 (2)°], so that their carbonyl O atoms are on the other side of, and closer to the central plane, with distances from the plane of 1.743 (4) and 1.206 (4) Å. One benzoate group is disordered between two conformers, with occupancies of 86.9 (3) and 13.1 (3)%, related by a 143 (1)° rotation about the bond to the central benzene ring. The phenyl groups of the two conformers occupy the same space. The mol-ecule packs in the crystal with two of the three benzoate phenyl rings stacked parallel to symmetry-related counterparts, with perpendicular distances of 3.715 (5) and 3.791 (5) Å. The parallel rings are slipped away from each other, however, with centroid-centroid distances of 4.122 (2) and 4.363 (2) Å, respectively.

Related literature

For a review of structural features of specific dendrimers, see: Stadler (2010 ▶). For related crystal structures, see: Pigge et al. (2010 ▶); Shi & Zhang (2006 ▶); Sasvari & Parkanyi (1980 ▶). For related papers on the properties and synthesis of dendrimers, see: Monaco et al. (2013 ▶); Moore & Stupp (1990 ▶); Nagvekar & Gibson (1997 ▶).

Experimental

Crystal data

C27H18O6

M = 438.41

Monoclinic,

a = 23.128 (5) Å

b = 6.332 (2) Å

c = 15.030 (3) Å

β = 103.22 (2)°

V = 2142.8 (9) Å3

Z = 4

Mo Kα radiation

μ = 0.10 mm−1

T = 295 K

0.4 × 0.4 × 0.13 mm

Data collection

Enraf–Nonius CAD-4 diffractometer

4950 measured reflections

3775 independent reflections

2096 reflections with I > 2σ(I)

R int = 0.021

3 standard reflections every 120 min intensity decay: 0.5 (4)%

Refinement

R[F 2 > 2σ(F 2)] = 0.040

wR(F 2) = 0.114

S = 1.03

3775 reflections

295 parameters

2 restraints

H-atom parameters constrained

Δρmax = 0.15 e Å−3

Δρmin = −0.16 e Å−3

Data collection: CAD-4 Software (Enraf–Nonius, 1989 ▶); cell refinement: CAD-4 Software; data reduction followed procedures in Corfield et al. (1973 ▶) and data were averaged with a local version of SORTAV (Blessing, 1989 ▶); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: ORTEPIII (Burnett & Johnson, 1996 ▶); software used to prepare material for publication: SHELXL97.

Crystal structure: contains datablock(s) I. DOI: 10.1107/S1600536813031462/pk2503sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536813031462/pk2503Isup2.hkl

Click here for additional data file.

Supplementary material file. DOI: 10.1107/S1600536813031462/pk2503Isup3.cml

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

C27H18O6	F(000) = 912
Mr = 438.41	Dx = 1.359 Mg m−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71070 Å
Hall symbol: -P 2ybc	Cell parameters from 25 reflections
a = 23.128 (5) Å	θ = 3.6–20.3°
b = 6.332 (2) Å	µ = 0.10 mm−1
c = 15.030 (3) Å	T = 295 K
β = 103.22 (2)°	Plate cut from large crystal, colourless
V = 2142.8 (9) Å3	0.4 × 0.4 × 0.13 mm
Z = 4

Enraf–Nonius CAD-4 diffractometer	Rint = 0.021
Radiation source: fine-focus sealed tube	θmax = 25.0°, θmin = 1.8°
Graphite monochromator	h = −27→26
θ/2θ scans	k = 0→7
4950 measured reflections	l = 0→17
3775 independent reflections	3 standard reflections every 120 min
2096 reflections with I > 2σ(I)	intensity decay: 0.5(4)

Refinement on F2	Hydrogen site location: inferred from neighbouring sites
Least-squares matrix: full	H-atom parameters constrained
R[F2 > 2σ(F2)] = 0.040	w = 1/[σ2(Fo2) + (0.P)2 + 0.450P] where P = (Fo2 + 2Fc2)/3
wR(F2) = 0.114	(Δ/σ)max < 0.001
S = 1.03	Δρmax = 0.15 e Å−3
3775 reflections	Δρmin = −0.16 e Å−3
295 parameters	Extinction correction: SHELXL97 (Sheldrick, 2008), Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4
2 restraints	Extinction coefficient: 0.0067 (7)
Primary atom site location: structure-invariant direct methods

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)
O1	0.35661 (7)	0.5340 (3)	0.49441 (10)	0.0470 (4)
O2	0.15556 (7)	0.3414 (3)	0.35077 (11)	0.0486 (4)
O3	0.24069 (7)	0.9621 (3)	0.25815 (12)	0.0538 (5)
O4	0.37050 (8)	0.2080 (3)	0.44526 (14)	0.0740 (6)
O5	0.11874 (8)	0.5541 (3)	0.44322 (14)	0.0719 (6)
C1	0.30356 (10)	0.5610 (4)	0.42800 (15)	0.0405 (6)
C2	0.25623 (10)	0.4259 (4)	0.42122 (16)	0.0438 (6)
H2	0.2590	0.3050	0.4571	0.053*
C3	0.20481 (10)	0.4767 (4)	0.35957 (16)	0.0421 (6)
C4	0.19981 (10)	0.6514 (4)	0.30364 (16)	0.0436 (6)
H4	0.1646	0.6809	0.2614	0.052*
C5	0.24860 (10)	0.7809 (4)	0.31228 (15)	0.0416 (6)
C6	0.30092 (10)	0.7405 (4)	0.37541 (15)	0.0429 (6)
H6	0.3333	0.8312	0.3822	0.051*
C7	0.38779 (10)	0.3519 (4)	0.49572 (17)	0.0455 (6)
C8	0.11408 (10)	0.3985 (4)	0.39679 (17)	0.0466 (6)
C10	0.44494 (5)	0.3584 (3)	0.56490 (10)	0.0428 (6)
C11	0.47896 (7)	0.1775 (2)	0.57685 (11)	0.0577 (7)
H11	0.4646	0.0550	0.5453	0.069*
C12	0.53426 (7)	0.1781 (3)	0.63561 (13)	0.0669 (8)
H12	0.5572	0.0560	0.6437	0.080*
C13	0.55554 (6)	0.3595 (3)	0.68242 (11)	0.0650 (8)
H13	0.5929	0.3599	0.7221	0.078*
C14	0.52152 (7)	0.5404 (3)	0.67047 (11)	0.0642 (8)
H14	0.5359	0.6629	0.7021	0.077*
C15	0.46622 (7)	0.5399 (2)	0.61171 (12)	0.0551 (7)
H15	0.4433	0.6620	0.6036	0.066*
C16	0.06392 (6)	0.2479 (2)	0.38278 (11)	0.0440 (6)
C17	0.06666 (6)	0.0496 (3)	0.34617 (11)	0.0513 (7)
H17	0.1011	0.0056	0.3296	0.062*
C18	0.01834 (8)	−0.0835 (2)	0.33404 (12)	0.0607 (8)
H18	0.0202	−0.2173	0.3093	0.073*
C19	−0.03272 (7)	−0.0183 (3)	0.35852 (13)	0.0720 (9)
H19	−0.0653	−0.1081	0.3503	0.086*
C20	−0.03546 (6)	0.1800 (3)	0.39513 (13)	0.0749 (9)
H20	−0.0699	0.2239	0.4116	0.090*
C21	0.01286 (7)	0.3131 (2)	0.40725 (12)	0.0599 (8)
H21	0.0110	0.4469	0.4320	0.072*
C22A	0.26207 (19)	1.2348 (5)	0.1664 (2)	0.0428 (10)	0.869 (3)
C23A	0.30488 (14)	1.3733 (8)	0.1497 (2)	0.0522 (9)	0.869 (3)
H23A	0.3449	1.3461	0.1738	0.063*	0.869 (3)
C24A	0.2879 (2)	1.5522 (7)	0.0970 (3)	0.0608 (9)	0.869 (3)
H24A	0.3165	1.6471	0.0872	0.073*	0.869 (3)
C25A	0.2294 (3)	1.5889 (6)	0.0596 (3)	0.0573 (9)	0.869 (3)
H25A	0.2183	1.7081	0.0236	0.069*	0.869 (3)
C26A	0.18673 (18)	1.4519 (10)	0.0746 (3)	0.0561 (9)	0.869 (3)
H26A	0.1470	1.4774	0.0478	0.067*	0.869 (3)
C27A	0.20245 (17)	1.2766 (7)	0.1291 (3)	0.0487 (10)	0.869 (3)
H27A	0.1733	1.1866	0.1408	0.058*	0.869 (3)
C9A	0.28368 (12)	1.0471 (5)	0.22254 (18)	0.0428 (7)	0.869 (3)
O6A	0.33266 (8)	0.9761 (4)	0.23489 (14)	0.0620 (7)	0.869 (3)
C27B	0.2213 (18)	1.234 (3)	0.1497 (18)	0.0487 (10)	0.131 (3)
C22B	0.2801 (15)	1.294 (4)	0.1727 (14)	0.0428 (10)	0.131 (3)
H22B	0.3076	1.2125	0.2132	0.051*	0.131 (3)
C23B	0.2982 (8)	1.475 (5)	0.136 (2)	0.0522 (9)	0.131 (3)
H23B	0.3379	1.5149	0.1511	0.063*	0.131 (3)
C24B	0.2575 (17)	1.595 (3)	0.0756 (18)	0.0608 (9)	0.131 (3)
H24B	0.2697	1.7173	0.0506	0.073*	0.131 (3)
C25B	0.1986 (14)	1.536 (4)	0.0526 (14)	0.0573 (9)	0.131 (3)
H25B	0.1711	1.6174	0.0121	0.069*	0.131 (3)
C26B	0.1805 (8)	1.355 (5)	0.090 (2)	0.0561 (9)	0.131 (3)
H26B	0.1408	1.3150	0.0742	0.067*	0.131 (3)
O6B	0.1535 (6)	0.978 (2)	0.1877 (11)	0.077 (5)	0.131 (3)
C9B	0.1998 (8)	1.048 (3)	0.1964 (12)	0.059 (6)*	0.131 (3)

	U11	U22	U33	U12	U13	U23
O1	0.0475 (9)	0.0382 (10)	0.0499 (10)	0.0048 (8)	0.0003 (8)	0.0000 (8)
O2	0.0472 (9)	0.0429 (10)	0.0581 (10)	−0.0123 (9)	0.0169 (8)	−0.0070 (9)
O3	0.0517 (10)	0.0453 (11)	0.0634 (11)	0.0024 (9)	0.0110 (9)	0.0177 (9)
O4	0.0591 (12)	0.0552 (13)	0.0993 (16)	0.0053 (10)	0.0007 (11)	−0.0290 (12)
O5	0.0679 (12)	0.0612 (13)	0.0925 (15)	−0.0157 (10)	0.0308 (11)	−0.0328 (12)
C1	0.0396 (13)	0.0417 (15)	0.0382 (13)	0.0046 (11)	0.0044 (10)	−0.0013 (12)
C2	0.0507 (15)	0.0372 (14)	0.0445 (13)	−0.0026 (12)	0.0130 (11)	0.0032 (12)
C3	0.0413 (13)	0.0388 (14)	0.0464 (14)	−0.0048 (12)	0.0106 (11)	−0.0036 (12)
C4	0.0388 (13)	0.0474 (15)	0.0432 (14)	0.0005 (12)	0.0064 (10)	−0.0012 (13)
C5	0.0421 (14)	0.0372 (14)	0.0458 (14)	0.0020 (11)	0.0104 (11)	0.0058 (12)
C6	0.0429 (13)	0.0395 (15)	0.0457 (13)	−0.0029 (12)	0.0091 (11)	0.0012 (12)
C7	0.0461 (14)	0.0397 (15)	0.0522 (15)	−0.0017 (13)	0.0141 (12)	−0.0001 (13)
C8	0.0441 (14)	0.0472 (17)	0.0472 (14)	−0.0001 (12)	0.0075 (12)	−0.0017 (13)
C10	0.0406 (13)	0.0410 (15)	0.0482 (14)	0.0024 (12)	0.0128 (11)	0.0026 (12)
C11	0.0518 (16)	0.0458 (17)	0.0748 (19)	0.0068 (13)	0.0128 (14)	0.0017 (15)
C12	0.0577 (18)	0.060 (2)	0.080 (2)	0.0194 (16)	0.0112 (15)	0.0102 (17)
C13	0.0492 (16)	0.082 (2)	0.0601 (17)	0.0045 (17)	0.0057 (14)	0.0026 (17)
C14	0.0582 (17)	0.062 (2)	0.0667 (18)	−0.0016 (16)	0.0022 (14)	−0.0092 (16)
C15	0.0545 (16)	0.0495 (17)	0.0576 (16)	0.0083 (14)	0.0051 (13)	−0.0015 (14)
C16	0.0443 (14)	0.0437 (16)	0.0423 (13)	−0.0037 (12)	0.0065 (11)	0.0015 (12)
C17	0.0471 (15)	0.0463 (17)	0.0584 (16)	−0.0013 (13)	0.0076 (12)	0.0043 (14)
C18	0.0631 (18)	0.0492 (18)	0.0644 (18)	−0.0142 (15)	0.0033 (15)	−0.0014 (15)
C19	0.0600 (18)	0.080 (2)	0.074 (2)	−0.0318 (18)	0.0125 (15)	0.0009 (18)
C20	0.0544 (17)	0.091 (3)	0.085 (2)	−0.0153 (18)	0.0282 (16)	−0.002 (2)
C21	0.0575 (16)	0.0639 (19)	0.0622 (17)	−0.0062 (15)	0.0220 (14)	−0.0067 (15)
C22A	0.052 (3)	0.038 (2)	0.0378 (14)	0.0008 (15)	0.0095 (14)	0.0018 (14)
C23A	0.0564 (19)	0.047 (2)	0.0508 (18)	−0.006 (2)	0.0064 (15)	0.0091 (19)
C24A	0.073 (3)	0.048 (2)	0.059 (2)	−0.010 (2)	0.010 (2)	0.0138 (18)
C25A	0.075 (3)	0.045 (2)	0.0516 (18)	0.0102 (19)	0.015 (2)	0.0108 (16)
C26A	0.0589 (18)	0.058 (3)	0.0516 (19)	0.0195 (19)	0.0123 (15)	0.004 (2)
C27A	0.049 (2)	0.0471 (19)	0.052 (2)	0.0086 (18)	0.0165 (19)	0.0037 (17)
C9A	0.0424 (16)	0.0424 (17)	0.0438 (16)	−0.0015 (15)	0.0103 (13)	0.0017 (14)
O6A	0.0471 (13)	0.0663 (16)	0.0751 (15)	0.0141 (11)	0.0191 (11)	0.0256 (12)
C27B	0.049 (2)	0.0471 (19)	0.052 (2)	0.0086 (18)	0.0165 (19)	0.0037 (17)
C22B	0.052 (3)	0.038 (2)	0.0378 (14)	0.0008 (15)	0.0095 (14)	0.0018 (14)
C23B	0.0564 (19)	0.047 (2)	0.0508 (18)	−0.006 (2)	0.0064 (15)	0.0091 (19)
C24B	0.073 (3)	0.048 (2)	0.059 (2)	−0.010 (2)	0.010 (2)	0.0138 (18)
C25B	0.075 (3)	0.045 (2)	0.0516 (18)	0.0102 (19)	0.015 (2)	0.0108 (16)
C26B	0.0589 (18)	0.058 (3)	0.0516 (19)	0.0195 (19)	0.0123 (15)	0.004 (2)
O6B	0.042 (8)	0.069 (11)	0.119 (13)	−0.003 (8)	0.017 (8)	0.032 (10)

O1—C7	1.357 (3)	C17—H17	0.9300
O1—C1	1.404 (3)	C18—C19	1.3780
O2—C8	1.354 (3)	C18—H18	0.9300
O2—C3	1.407 (3)	C19—C20	1.3780
O3—C9B	1.285 (15)	C19—H19	0.9300
O3—C5	1.394 (3)	C20—C21	1.3780
O3—C9A	1.345 (3)	C20—H20	0.9300
O4—C7	1.194 (3)	C21—H21	0.9300
O5—C8	1.198 (3)	C22A—C23A	1.388 (4)
C1—C6	1.378 (3)	C22A—C27A	1.390 (4)
C1—C2	1.374 (3)	C22A—C9A	1.477 (4)
C2—C3	1.368 (3)	C23A—C24A	1.386 (4)
C2—H2	0.9300	C23A—H23A	0.9300
C3—C4	1.378 (3)	C24A—C25A	1.362 (5)
C4—C5	1.377 (3)	C24A—H24A	0.9300
C4—H4	0.9300	C25A—C26A	1.371 (5)
C5—C6	1.380 (3)	C25A—H25A	0.9300
C6—H6	0.9300	C26A—C27A	1.378 (5)
C7—C10	1.484 (3)	C26A—H26A	0.9300
C8—C16	1.479 (3)	C27A—H27A	0.9300
C10—C11	1.3780	C9A—O6A	1.193 (3)
C10—C15	1.3781	C27B—C22B	1.3780
C11—C12	1.3780	C27B—C26B	1.3781
C11—H11	0.9300	C27B—C9B	1.514 (16)
C12—C13	1.3780	C22B—C23B	1.3780
C12—H12	0.9300	C22B—H22B	0.9300
C13—C14	1.3780	C23B—C24B	1.3780
C13—H13	0.9300	C23B—H23B	0.9300
C14—C15	1.3781	C24B—C25B	1.3780
C14—H14	0.9300	C24B—H24B	0.9300
C15—H15	0.9300	C25B—C26B	1.3780
C16—C17	1.3780	C25B—H25B	0.9300
C16—C21	1.3781	C26B—H26B	0.9300
C17—C18	1.3780	O6B—C9B	1.14 (2)
C7—O1—C1	119.26 (19)	C19—C18—H18	120.0
C8—O2—C3	116.22 (19)	C17—C18—H18	120.0
C9B—O3—C5	138.3 (9)	C20—C19—C18	120.0
C9B—O3—C9A	91.9 (8)	C20—C19—H19	120.0
C5—O3—C9A	123.5 (2)	C18—C19—H19	120.0
C6—C1—C2	122.7 (2)	C21—C20—C19	120.0
C6—C1—O1	115.2 (2)	C21—C20—H20	120.0
C2—C1—O1	121.9 (2)	C19—C20—H20	120.0
C1—C2—C3	117.3 (2)	C20—C21—C16	120.0
C1—C2—H2	121.4	C20—C21—H21	120.0
C3—C2—H2	121.4	C16—C21—H21	120.0
C4—C3—C2	122.7 (2)	C23A—C22A—C27A	119.3 (3)
C4—C3—O2	118.6 (2)	C23A—C22A—C9A	116.7 (4)
C2—C3—O2	118.7 (2)	C27A—C22A—C9A	124.0 (4)
C3—C4—C5	117.9 (2)	C22A—C23A—C24A	120.0 (3)
C3—C4—H4	121.1	C22A—C23A—H23A	120.0
C5—C4—H4	121.1	C24A—C23A—H23A	120.0
C4—C5—C6	121.7 (2)	C25A—C24A—C23A	120.0 (3)
C4—C5—O3	116.1 (2)	C25A—C24A—H24A	120.0
C6—C5—O3	122.1 (2)	C23A—C24A—H24A	120.0
C1—C6—C5	117.7 (2)	C24A—C25A—C26A	120.6 (3)
C1—C6—H6	121.2	C24A—C25A—H25A	119.7
C5—C6—H6	121.2	C26A—C25A—H25A	119.7
O4—C7—O1	122.6 (2)	C25A—C26A—C27A	120.3 (3)
O4—C7—C10	125.5 (2)	C25A—C26A—H26A	119.8
O1—C7—C10	111.8 (2)	C27A—C26A—H26A	119.8
O5—C8—O2	122.5 (2)	C22A—C27A—C26A	119.7 (3)
O5—C8—C16	125.2 (2)	C22A—C27A—H27A	120.1
O2—C8—C16	112.3 (2)	C26A—C27A—H27A	120.1
C11—C10—C15	120.0	O6A—C9A—O3	123.3 (3)
C11—C10—C7	117.32 (15)	O6A—C9A—C22A	125.3 (3)
C15—C10—C7	122.53 (15)	O3—C9A—C22A	111.4 (3)
C12—C11—C10	120.0	C22B—C27B—C26B	120.0
C12—C11—H11	120.0	C22B—C27B—C9B	121 (3)
C10—C11—H11	120.0	C26B—C27B—C9B	119 (3)
C11—C12—C13	120.0	C27B—C22B—C23B	120.0
C11—C12—H12	120.0	C27B—C22B—H22B	120.0
C13—C12—H12	120.0	C23B—C22B—H22B	120.0
C12—C13—C14	120.0	C24B—C23B—C22B	120.0
C12—C13—H13	120.0	C24B—C23B—H23B	120.0
C14—C13—H13	120.0	C22B—C23B—H23B	120.0
C15—C14—C13	120.0	C25B—C24B—C23B	120.0
C15—C14—H14	120.0	C25B—C24B—H24B	120.0
C13—C14—H14	120.0	C23B—C24B—H24B	120.0
C14—C15—C10	120.0	C24B—C25B—C26B	120.0
C14—C15—H15	120.0	C24B—C25B—H25B	120.0
C10—C15—H15	120.0	C26B—C25B—H25B	120.0
C17—C16—C21	120.0	C25B—C26B—C27B	120.0
C17—C16—C8	122.56 (15)	C25B—C26B—H26B	120.0
C21—C16—C8	117.44 (15)	C27B—C26B—H26B	120.0
C16—C17—C18	120.0	O6B—C9B—O3	115.8 (15)
C16—C17—H17	120.0	O6B—C9B—C27B	131 (2)
C18—C17—H17	120.0	O3—C9B—C27B	114 (2)
C19—C18—C17	120.0
C6—C1—O1—C7	−125.2 (2)	C4—C5—O3—C9A	−146.3 (2)
C1—O1—C7—O4	−3.8 (4)	C4—C5—O3—C9B	−3.1 (15)
C1—O1—C7—C10	175.05 (18)	C5—O3—C9A—O6A	−0.8 (4)
O1—C7—C10—C11	175.99 (15)	C5—O3—C9A—C22A	178.6 (2)
O1—C7—C10—C15	−8.5 (2)	C5—O3—C9B—O6B	12 (3)
C2—C3—O2—C8	98.2 (3)	C5—O3—C9B—C22B	−169.2 (9)
C3—O2—C8—O5	−0.6 (3)	O3—C9A—C22A—C23A	160.5 (3)
C3—O2—C8—C16	179.54 (18)	O3—C9A—C22A—C27A	−20.7 (4)
O2—C8—C16—C17	14.8 (3)	O3—C9B—C27B—C26B	−172.6 (13)
O2—C8—C16—C21	−164.75 (15)	O3—C9B—C27B—C22B	2 (2)