1,6-Di­benzoyl­oxy-2:4,3:5-O²:O⁴,O³:O⁵-bis­(phenyl­boronoyl­oxy)-D-mannitol

The title compound, C₃₂H₂₈B₂O₈, was obtained by the condensation of 1,6-di­benzoyl­oxy-D-mannitol with two equivalents of phenyl­boronic acid. The crystal structure confirms that the phenyl­boronate moieties exist as six-membered rings in the solid state.

Key indicators

• Single-crystal X-ray study
• T = 123 K
• Mean [sigma](C-C) = 0.005 Å
• R factor = 0.060
• wR factor = 0.097
• Data-to-parameter ratio = 10.4

checkCIF results

No syntax errors found

ADDSYM reports no extra symmetry


 Alert Level C:



RINTA_01  Alert C The value of Rint is greater than 0.10
          Rint given   0.128

General Notes



REFLT_03
         From the CIF: _diffrn_reflns_theta_max           28.40
         From the CIF: _reflns_number_total               3926
         Count of symmetry unique reflns         3980
         Completeness (_total/calc)             98.64%
         TEST3: Check Friedels for noncentro structure
         Estimate of Friedel pairs measured         0
         Fraction of Friedel pairs measured     0.000
         Are heavy atom types Z>Si present           no
          Please check that the estimate of the number of Friedel pairs is
          correct. If it is not, please give the correct count in the
          _publ_section_exptl_refinement section of the submitted CIF.


 0 Alert Level A = Potentially serious problem

 0 Alert Level B = Potential problem

 1 Alert Level C = Please check

---

Computing details

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

D-Mannitol 1,6-dibenzoate-2:4, 3:5-O2:O4, O3:O5 bis(phenylboronate)

Crystal data

C32H28B2O8	F(000) = 1176
Mr = 562.16	Dx = 1.338 Mg m^−3
Orthorhombic, P212121	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: P 2ac 2ab	Cell parameters from 33223 reflections
a = 5.9646 (1) Å	µ = 0.09 mm^−1
b = 18.0749 (3) Å	T = 123 K
c = 25.8911 (6) Å	Needle, colourless
V = 2791.31 (9) Å^3	0.25 × 0.15 × 0.08 mm
Z = 4

Data collection

Nonius KappaCCD diffractometer	2524 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	Rint = 0.128
Graphite monochromator	θmax = 28.4°, θmin = 2.4°
CCD rotation images, thick slices scans	h = −7→7
33146 measured reflections	k = −24→24
3926 independent reflections	l = −34→34

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)] = 0.060	H atoms treated by a mixture of independent and constrained refinement
wR(F^2) = 0.097	w = 1/[σ^2(Fo^2) + (0.0263P)^2 + 1.1628P] where P = (Fo^2 + 2Fc^2)/3
S = 1.05	(Δ/σ)max < 0.001
3926 reflections	Δρmax = 0.28 e Å^−3
379 parameters	Δρmin = −0.29 e Å^−3
0 restraints	Absolute structure: unk
Primary atom site location: structure-invariant direct methods

Special details

Experimental. ¹H n.m.r. (300 MHz, d₆-DMSO): δ 4.59–4.72 (4H, m, 2 x CH2—CH(OBPh)), 4.76–4.83 (2H, m, 2 x CH2—CH(OBPh)), 4.94–4.99 (2H, br s, 2 x CH(OBPh)CH(OBPh)CH2), 7.26–7.98 (20H, m, ArH)

¹³C n.m.r. (75 MHz, d₆-DMSO): 64.2, 65.9, 72.1, 127.5, 128.4, 129.2, 129.5, 131.2, 133.2, 134.0, 165.9.

¹¹B n.m.r. (160 MHz, CDCl₃): δ 30 (broad).

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.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Ų)

	x	y	z	Uiso*/Ueq
C1	0.6356 (5)	0.56895 (18)	0.18654 (13)	0.0179 (8)
H1A	0.7925	0.5863	0.1897	0.022*
H1B	0.5467	0.6087	0.1700	0.022*
C2	0.6278 (6)	0.49984 (17)	0.15344 (12)	0.0165 (8)
H2	0.4686	0.4826	0.1522	0.020*
C3	0.7031 (5)	0.51494 (18)	0.09796 (12)	0.0140 (7)
H3	0.6444	0.5642	0.0868	0.017*
C4	0.9555 (5)	0.51404 (17)	0.09170 (12)	0.0148 (7)
H4	1.0202	0.5579	0.1099	0.018*
C5	1.0245 (5)	0.51672 (16)	0.03513 (12)	0.0156 (7)
H5	1.1868	0.5033	0.0328	0.019*
C6	0.9927 (5)	0.59224 (16)	0.01037 (13)	0.0168 (8)
H6A	1.0630	0.5926	−0.0243	0.020*
H6B	0.8306	0.6024	0.0061	0.020*
C7	1.0776 (6)	0.35153 (17)	0.18262 (12)	0.0181 (7)
C8	1.2917 (6)	0.32908 (18)	0.16691 (14)	0.0208 (8)
H8	1.3667	0.3557	0.1404	0.025*
C9	1.3954 (6)	0.26877 (18)	0.18945 (14)	0.0269 (9)
H9	1.5408	0.2545	0.1783	0.032*
C10	1.2896 (7)	0.2293 (2)	0.22785 (15)	0.0342 (10)
H10	1.3620	0.1880	0.2432	0.041*
C11	1.0768 (7)	0.2501 (2)	0.24397 (15)	0.0344 (10)
H11	1.0018	0.2226	0.2700	0.041*
C12	0.9744 (6)	0.31105 (19)	0.22196 (13)	0.0263 (9)
H12	0.8305	0.3257	0.2339	0.032*
C13	0.5660 (6)	0.38108 (16)	−0.01258 (12)	0.0151 (7)
C14	0.6418 (6)	0.35652 (18)	−0.06049 (13)	0.0204 (8)
H14	0.7821	0.3735	−0.0732	0.025*
C15	0.5159 (6)	0.30764 (18)	−0.09010 (14)	0.0248 (9)
H15	0.5697	0.2919	−0.1228	0.030*
C16	0.3120 (6)	0.28185 (19)	−0.07192 (14)	0.0267 (9)
H16	0.2264	0.2483	−0.0921	0.032*
C17	0.2330 (6)	0.30495 (17)	−0.02438 (14)	0.0223 (8)
H17	0.0932	0.2872	−0.0119	0.027*
C18	0.3584 (5)	0.35428 (17)	0.00514 (13)	0.0181 (8)
H18	0.3030	0.3701	0.0377	0.022*
C19	0.3193 (5)	0.54825 (19)	0.24077 (13)	0.0189 (8)
C20	0.2481 (6)	0.52827 (17)	0.29406 (13)	0.0160 (8)
C21	0.0374 (6)	0.49609 (18)	0.30079 (14)	0.0226 (8)
H21	−0.0583	0.4888	0.2719	0.027*
C22	−0.0322 (6)	0.47475 (19)	0.34953 (14)	0.0265 (9)
H22	−0.1740	0.4516	0.3540	0.032*
C23	0.1049 (7)	0.48711 (19)	0.39185 (14)	0.0267 (9)
H23	0.0566	0.4726	0.4253	0.032*
C24	0.3127 (6)	0.52063 (19)	0.38555 (14)	0.0252 (9)
H24	0.4047	0.5301	0.4148	0.030*
C25	0.3854 (6)	0.54021 (18)	0.33680 (12)	0.0211 (8)
H25	0.5293	0.5619	0.3324	0.025*
C26	1.3177 (5)	0.65965 (18)	0.03750 (13)	0.0173 (8)
C27	1.4023 (6)	0.71521 (17)	0.07521 (13)	0.0168 (7)
C28	1.6158 (6)	0.74425 (17)	0.06735 (14)	0.0216 (8)
H28	1.7030	0.7282	0.0388	0.026*
C29	1.7013 (6)	0.79650 (19)	0.10114 (14)	0.0266 (9)
H29	1.8456	0.8172	0.0953	0.032*
C30	1.5760 (7)	0.8186 (2)	0.14344 (14)	0.0313 (9)
H30	1.6351	0.8538	0.1670	0.038*
C31	1.3642 (7)	0.7891 (2)	0.15134 (15)	0.0336 (10)
H31	1.2785	0.8044	0.1804	0.040*
C32	1.2764 (6)	0.73772 (19)	0.11739 (14)	0.0273 (9)
H32	1.1308	0.7179	0.1229	0.033*
B1	0.9566 (7)	0.4177 (2)	0.15669 (15)	0.0165 (9)
B2	0.6992 (6)	0.4374 (2)	0.02087 (15)	0.0160 (8)
O1	0.7586 (4)	0.44259 (11)	0.17727 (8)	0.0170 (5)
O2	1.0503 (4)	0.44781 (11)	0.11329 (8)	0.0158 (5)
O3	0.6032 (4)	0.45851 (11)	0.06679 (8)	0.0180 (5)
O4	0.8990 (4)	0.46534 (11)	0.00414 (8)	0.0177 (5)
O5	0.5455 (4)	0.55300 (12)	0.23746 (8)	0.0169 (5)
O6	0.1954 (4)	0.55903 (14)	0.20475 (9)	0.0246 (6)
O7	1.0933 (4)	0.64946 (11)	0.04231 (9)	0.0177 (5)
O8	1.4314 (4)	0.62669 (12)	0.00645 (9)	0.0240 (6)

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
C1	0.0186 (18)	0.0201 (18)	0.0150 (19)	−0.0019 (15)	0.0016 (14)	−0.0004 (15)
C2	0.0179 (18)	0.0172 (18)	0.0144 (18)	0.0010 (15)	−0.0009 (14)	0.0023 (14)
C3	0.0153 (17)	0.0144 (16)	0.0124 (18)	0.0005 (15)	0.0006 (14)	−0.0012 (14)
C4	0.0160 (18)	0.0135 (17)	0.0150 (18)	0.0010 (15)	−0.0002 (14)	0.0000 (14)
C5	0.0148 (18)	0.0151 (17)	0.0167 (19)	−0.0031 (15)	−0.0008 (15)	−0.0021 (15)
C6	0.0160 (18)	0.0175 (17)	0.0168 (19)	−0.0034 (15)	−0.0014 (14)	0.0002 (15)
C7	0.0222 (19)	0.0167 (17)	0.0155 (19)	−0.0013 (17)	−0.0013 (15)	−0.0023 (14)
C8	0.0231 (19)	0.0161 (18)	0.023 (2)	0.0000 (16)	−0.0012 (16)	−0.0008 (15)
C9	0.025 (2)	0.027 (2)	0.028 (2)	0.0080 (18)	−0.0001 (18)	−0.0010 (18)
C10	0.044 (3)	0.029 (2)	0.030 (2)	0.015 (2)	−0.003 (2)	0.0104 (19)
C11	0.044 (3)	0.033 (2)	0.026 (2)	0.008 (2)	0.008 (2)	0.0149 (18)
C12	0.028 (2)	0.030 (2)	0.022 (2)	0.0063 (18)	0.0024 (17)	0.0059 (17)
C13	0.0197 (18)	0.0133 (16)	0.0123 (19)	0.0024 (15)	−0.0029 (15)	0.0014 (14)
C14	0.023 (2)	0.0191 (18)	0.019 (2)	−0.0007 (16)	−0.0003 (15)	0.0016 (16)
C15	0.027 (2)	0.024 (2)	0.023 (2)	0.0020 (17)	−0.0028 (17)	−0.0083 (16)
C16	0.032 (2)	0.021 (2)	0.027 (2)	−0.0004 (18)	−0.0089 (19)	−0.0059 (17)
C17	0.021 (2)	0.0177 (18)	0.028 (2)	−0.0026 (16)	−0.0029 (16)	0.0001 (16)
C18	0.0204 (19)	0.0157 (17)	0.0181 (19)	0.0002 (15)	−0.0008 (15)	0.0004 (15)
C19	0.0167 (19)	0.0206 (19)	0.019 (2)	0.0003 (16)	0.0003 (16)	−0.0067 (16)
C20	0.0175 (19)	0.0168 (17)	0.0138 (18)	0.0047 (15)	0.0008 (14)	−0.0026 (14)
C21	0.0177 (19)	0.029 (2)	0.021 (2)	0.0014 (17)	−0.0001 (16)	0.0030 (16)
C22	0.025 (2)	0.029 (2)	0.025 (2)	0.0025 (18)	0.0088 (17)	0.0016 (17)
C23	0.035 (2)	0.027 (2)	0.018 (2)	0.0060 (19)	0.0059 (18)	0.0021 (17)
C24	0.030 (2)	0.028 (2)	0.018 (2)	0.0013 (18)	−0.0028 (17)	−0.0013 (17)
C25	0.0233 (19)	0.0263 (19)	0.0137 (19)	0.0021 (17)	0.0012 (16)	−0.0013 (15)
C26	0.0172 (19)	0.0168 (18)	0.0178 (19)	0.0025 (15)	0.0000 (16)	0.0063 (15)
C27	0.0180 (18)	0.0163 (17)	0.0160 (19)	0.0021 (16)	−0.0023 (15)	0.0039 (15)
C28	0.024 (2)	0.0158 (17)	0.025 (2)	−0.0008 (17)	0.0000 (17)	0.0022 (16)
C29	0.025 (2)	0.023 (2)	0.032 (2)	−0.0049 (17)	−0.0034 (18)	0.0016 (17)
C30	0.041 (3)	0.027 (2)	0.026 (2)	−0.008 (2)	−0.009 (2)	−0.0039 (18)
C31	0.039 (3)	0.039 (2)	0.023 (2)	−0.008 (2)	0.0066 (18)	−0.0076 (19)
C32	0.029 (2)	0.029 (2)	0.025 (2)	−0.0093 (19)	0.0040 (18)	−0.0047 (18)
B1	0.021 (2)	0.0156 (19)	0.013 (2)	−0.0041 (17)	−0.0009 (17)	−0.0049 (16)
B2	0.016 (2)	0.016 (2)	0.016 (2)	0.0037 (17)	0.0006 (17)	0.0030 (17)
O1	0.0193 (13)	0.0174 (12)	0.0144 (13)	0.0037 (11)	0.0016 (10)	0.0026 (10)
O2	0.0158 (12)	0.0155 (11)	0.0161 (12)	0.0038 (11)	−0.0009 (10)	0.0038 (10)
O3	0.0155 (12)	0.0232 (12)	0.0152 (12)	−0.0041 (11)	−0.0003 (10)	−0.0074 (10)
O4	0.0205 (13)	0.0177 (12)	0.0148 (13)	−0.0033 (11)	0.0003 (11)	−0.0039 (10)
O5	0.0168 (13)	0.0228 (12)	0.0111 (13)	0.0029 (11)	0.0011 (10)	−0.0007 (10)
O6	0.0188 (13)	0.0400 (15)	0.0152 (13)	0.0022 (12)	−0.0038 (11)	0.0009 (12)
O7	0.0160 (12)	0.0155 (12)	0.0217 (13)	−0.0009 (11)	0.0010 (11)	0.0014 (10)
O8	0.0187 (13)	0.0274 (13)	0.0258 (15)	0.0016 (12)	0.0023 (12)	−0.0049 (11)

Geometric parameters (Å, º)

C1—O5	1.453 (4)	C16—C17	1.383 (5)
C1—C2	1.516 (4)	C16—H16	0.9500
C1—H1A	0.9900	C17—C18	1.392 (4)
C1—H1B	0.9900	C17—H17	0.9500
C2—O1	1.436 (4)	C18—H18	0.9500
C2—C3	1.530 (4)	C19—O6	1.206 (4)
C2—H2	1.0000	C19—O5	1.354 (4)
C3—O3	1.431 (4)	C19—C20	1.488 (4)
C3—C4	1.514 (5)	C20—C25	1.394 (4)
C3—H3	1.0000	C20—C21	1.396 (5)
C4—O2	1.437 (4)	C21—C22	1.383 (5)
C4—C5	1.522 (4)	C21—H21	0.9500
C4—H4	1.0000	C22—C23	1.385 (5)
C5—O4	1.438 (4)	C22—H22	0.9500
C5—C6	1.520 (4)	C23—C24	1.389 (5)
C5—H5	1.0000	C23—H23	0.9500
C6—O7	1.454 (4)	C24—C25	1.381 (5)
C6—H6A	0.9900	C24—H24	0.9500
C6—H6B	0.9900	C25—H25	0.9500
C7—C12	1.397 (4)	C26—O8	1.209 (4)
C7—C8	1.400 (5)	C26—O7	1.357 (4)
C7—B1	1.550 (5)	C26—C27	1.489 (5)
C8—C9	1.383 (5)	C27—C32	1.386 (5)
C8—H8	0.9500	C27—C28	1.393 (5)
C9—C10	1.377 (5)	C28—C29	1.385 (5)
C9—H9	0.9500	C28—H28	0.9500
C10—C11	1.388 (5)	C29—C30	1.384 (5)
C10—H10	0.9500	C29—H29	0.9500
C11—C12	1.383 (5)	C30—C31	1.386 (5)
C11—H11	0.9500	C30—H30	0.9500
C12—H12	0.9500	C31—C32	1.382 (5)
C13—C14	1.393 (4)	C31—H31	0.9500
C13—C18	1.406 (4)	C32—H32	0.9500
C13—B2	1.555 (5)	B1—O2	1.368 (4)
C14—C15	1.390 (4)	B1—O1	1.371 (4)
C14—H14	0.9500	B2—O4	1.365 (4)
C15—C16	1.385 (5)	B2—O3	1.374 (4)
C15—H15	0.9500
O5—C1—C2	109.8 (2)	C17—C16—C15	120.0 (3)
O5—C1—H1A	109.7	C17—C16—H16	120.0
C2—C1—H1A	109.7	C15—C16—H16	120.0
O5—C1—H1B	109.7	C16—C17—C18	119.9 (3)
C2—C1—H1B	109.7	C16—C17—H17	120.0
H1A—C1—H1B	108.2	C18—C17—H17	120.0
O1—C2—C1	109.5 (3)	C17—C18—C13	121.0 (3)
O1—C2—C3	111.9 (3)	C17—C18—H18	119.5
C1—C2—C3	112.0 (3)	C13—C18—H18	119.5
O1—C2—H2	107.7	O6—C19—O5	123.5 (3)
C1—C2—H2	107.7	O6—C19—C20	125.5 (3)
C3—C2—H2	107.7	O5—C19—C20	111.0 (3)
O3—C3—C4	110.3 (3)	C25—C20—C21	119.6 (3)
O3—C3—C2	106.3 (2)	C25—C20—C19	122.1 (3)
C4—C3—C2	113.0 (3)	C21—C20—C19	118.3 (3)
O3—C3—H3	109.1	C22—C21—C20	120.0 (3)
C4—C3—H3	109.1	C22—C21—H21	120.0
C2—C3—H3	109.1	C20—C21—H21	120.0
O2—C4—C3	111.0 (3)	C21—C22—C23	119.9 (4)
O2—C4—C5	107.1 (2)	C21—C22—H22	120.0
C3—C4—C5	111.8 (3)	C23—C22—H22	120.0
O2—C4—H4	108.9	C22—C23—C24	120.3 (3)
C3—C4—H4	108.9	C22—C23—H23	119.9
C5—C4—H4	108.9	C24—C23—H23	119.9
O4—C5—C6	106.2 (2)	C25—C24—C23	120.0 (3)
O4—C5—C4	112.1 (3)	C25—C24—H24	120.0
C6—C5—C4	113.6 (3)	C23—C24—H24	120.0
O4—C5—H5	108.2	C24—C25—C20	120.1 (3)
C6—C5—H5	108.2	C24—C25—H25	120.0
C4—C5—H5	108.2	C20—C25—H25	120.0
O7—C6—C5	110.3 (2)	O8—C26—O7	123.2 (3)
O7—C6—H6A	109.6	O8—C26—C27	125.4 (3)
C5—C6—H6A	109.6	O7—C26—C27	111.4 (3)
O7—C6—H6B	109.6	C32—C27—C28	120.0 (3)
C5—C6—H6B	109.6	C32—C27—C26	122.1 (3)
H6A—C6—H6B	108.1	C28—C27—C26	117.9 (3)
C12—C7—C8	117.5 (3)	C29—C28—C27	120.1 (4)
C12—C7—B1	121.0 (3)	C29—C28—H28	120.0
C8—C7—B1	121.5 (3)	C27—C28—H28	120.0
C9—C8—C7	120.9 (3)	C30—C29—C28	119.8 (4)
C9—C8—H8	119.5	C30—C29—H29	120.1
C7—C8—H8	119.5	C28—C29—H29	120.1
C10—C9—C8	120.6 (4)	C29—C30—C31	119.9 (4)
C10—C9—H9	119.7	C29—C30—H30	120.1
C8—C9—H9	119.7	C31—C30—H30	120.1
C9—C10—C11	119.7 (4)	C32—C31—C30	120.6 (4)
C9—C10—H10	120.2	C32—C31—H31	119.7
C11—C10—H10	120.2	C30—C31—H31	119.7
C12—C11—C10	119.7 (4)	C31—C32—C27	119.6 (4)
C12—C11—H11	120.1	C31—C32—H32	120.2
C10—C11—H11	120.1	C27—C32—H32	120.2
C11—C12—C7	121.5 (3)	O2—B1—O1	122.7 (3)
C11—C12—H12	119.2	O2—B1—C7	118.2 (3)
C7—C12—H12	119.2	O1—B1—C7	119.1 (3)
C14—C13—C18	117.8 (3)	O4—B2—O3	122.4 (3)
C14—C13—B2	122.6 (3)	O4—B2—C13	120.8 (3)
C18—C13—B2	119.6 (3)	O3—B2—C13	116.8 (3)
C15—C14—C13	121.2 (3)	B1—O1—C2	122.5 (3)
C15—C14—H14	119.4	B1—O2—C4	119.4 (3)
C13—C14—H14	119.4	B2—O3—C3	120.8 (3)
C16—C15—C14	120.1 (3)	B2—O4—C5	121.1 (3)
C16—C15—H15	120.0	C19—O5—C1	116.0 (3)
C14—C15—H15	120.0	C26—O7—C6	116.8 (3)