trans-5-(4-Bromo­benzoyl­oxy)-2-phenyl-1,3-dioxane

The structure of the major product from the treatment of benz­aldehyde with glycerol, derivatized as its crystalline 4-bromo­benzoate, is shown to be the title compound, C₁₇H₁₅BrO₄, by a room-temperature single-crystal X-ray structure determination, providing a rare example of a structurally characterized 1,3-dioxane system.

Key indicators

• Single-crystal X-ray study
• T = 300 K
• Mean [sigma](C-C) = 0.012 Å
• R factor = 0.054
• wR factor = 0.099
• Data-to-parameter ratio = 13.7

checkCIF/PLATON results

No syntax errors found



Alert level A
DIFF012_ALERT_1_A  _diffrn_reflns_av_R_equivalents is missing
            R factor for symmetry-equivalent intensities.
            The following tests will not be performed
            RINTA

Author Response: only a unique set of reflections were measured on the four-circle diffractometer.

Alert level C
PLAT026_ALERT_3_C Ratio Observed / Unique Reflections too Low ....         46 Perc.
PLAT242_ALERT_2_C Check Low    U(eq) as Compared to Neighbors ....        C54
PLAT341_ALERT_3_C Low Bond Precision on C-C bonds (x 1000) Ang ...         12
PLAT431_ALERT_2_C Short Inter HL..A Contact  Br54   ..  O50     ..       3.27 Ang.

   1 ALERT level A = In general: serious problem
   0 ALERT level B = Potentially serious problem
   4 ALERT level C = Check and explain
   0 ALERT level G = General alerts; check

   1 ALERT type 1 CIF construction/syntax error, inconsistent or missing data
   2 ALERT type 2 Indicator that the structure model may be wrong or deficient
   2 ALERT type 3 Indicator that the structure quality may be low
   0 ALERT type 4 Improvement, methodology, query or suggestion

---

Computing details

Data collection: Syntex Software (Syntex, 1974); cell refinement: Syntex Software; data reduction: Xtal3.5 (Hall et al., 1995); program(s) used to solve structure: Xtal3.5; program(s) used to refine structure: CRYLSQ in Xtal3.5; molecular graphics: Xtal3.5; software used to prepare material for publication: BONDLA and CIFIO in Xtal3.5.

(I)

Crystal data

C17H15BrO4	Z = 2
Mr = 363.22	F(000) = 368
Triclinic, P1	Dx = 1.517 Mg m^−3
Hall symbol: -p_1	Mo Kα radiation, λ = 0.71073 Å
a = 8.117 (4) Å	Cell parameters from 6 reflections
b = 9.977 (7) Å	θ = 9.0–12.7°
c = 10.737 (6) Å	µ = 2.6 mm^−1
α = 113.47 (4)°	T = 300 K
β = 90.49 (4)°	Plate, colourless
γ = 93.98 (5)°	0.4 × 0.21 × 0.09 mm
V = 795.0 (9) Å^3

Data collection

Syntex P1 diffractometer	1251 reflections with I > 2.00 σ(I)
Radiation source: sealed tube	θmax = 25.0°, θmin = 2.1°
Graphite monochromator	h = −9→0
2θ–ω scans	k = −10→10
Absorption correction: gaussian Xtal, absorb	l = −11→11
Tmin = 0.55, Tmax = 0.81	9 standard reflections every 60 min
2718 measured reflections	intensity decay: none
2718 independent reflections

Refinement

Refinement on F^2	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Secondary atom site location: absorb
R[F^2 > 2σ(F^2)] = 0.054	Hydrogen site location: absorb
wR(F^2) = 0.099	H-atom parameters not refined
S = 1.17	w = 1/(σ^2(F^2) + 2.4F^2)
2718 reflections	(Δ/σ)max = 0.002
199 parameters	Δρmax = 1.27 e Å^−3
0 restraints	Δρmin = −0.86 e Å^−3
0 constraints

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

	x	y	z	Uiso*/Ueq
O1	0.3823 (7)	0.8050 (5)	0.6911 (5)	0.060 (3)
C2	0.3537 (8)	0.8534 (7)	0.8302 (7)	0.048 (3)
O3	0.2062 (7)	0.7854 (5)	0.8517 (5)	0.065 (3)
C4	0.2126 (11)	0.6301 (8)	0.7997 (9)	0.071 (5)
C5	0.2436 (9)	0.5723 (7)	0.6491 (8)	0.052 (4)
C6	0.3987 (11)	0.6507 (8)	0.6291 (8)	0.063 (4)
C21	0.3413 (8)	1.0155 (7)	0.8855 (7)	0.044 (3)
C22	0.4401 (11)	1.1028 (8)	0.8417 (8)	0.065 (4)
C23	0.4299 (14)	1.2539 (9)	0.8948 (10)	0.086 (6)
C24	0.3158 (13)	1.3167 (9)	0.9915 (10)	0.079 (5)
C25	0.2219 (12)	1.2317 (9)	1.0387 (10)	0.076 (5)
C26	0.2327 (9)	1.0828 (8)	0.9860 (8)	0.060 (4)
O5	0.2572 (6)	0.4163 (5)	0.6015 (5)	0.054 (3)
C50	0.1962 (9)	0.3356 (7)	0.4726 (7)	0.048 (3)
O50	0.1510 (7)	0.3875 (5)	0.3978 (5)	0.059 (3)
C51	0.1924 (9)	0.1747 (7)	0.4390 (7)	0.048 (3)
C52	0.1059 (10)	0.0805 (8)	0.3226 (8)	0.060 (4)
C53	0.0990 (11)	−0.0683 (8)	0.2849 (8)	0.067 (5)
C54	0.1786 (10)	−0.1224 (7)	0.3665 (8)	0.056 (4)
Br54	0.17153 (14)	−0.32652 (9)	0.31957 (12)	0.0832 (6)
C55	0.2660 (11)	−0.0307 (8)	0.4835 (8)	0.066 (5)
C56	0.2712 (10)	0.1178 (8)	0.5192 (8)	0.060 (4)
H2	0.44565	0.82539	0.87340	0.05800*
H4a	0.11249	0.58471	0.81355	0.07800*
H4b	0.30185	0.60645	0.84433	0.07800*
H5	0.15521	0.59026	0.60001	0.05900*
H6a	0.48936	0.62740	0.67107	0.07000*
H6b	0.41477	0.62125	0.53521	0.07000*
H22	0.52007	1.05967	0.77465	0.07300*
H23	0.49598	1.31187	0.85987	0.10200*
H24	0.30848	1.41913	1.02593	0.09300*
H25	0.15069	1.27582	1.10987	0.08800*
H26	0.16199	1.02319	1.01599	0.07200*
H52	0.05122	0.12197	0.26925	0.07000*
H53	0.04107	−0.13262	0.20424	0.07700*
H55	0.31790	−0.06923	0.53893	0.07800*
H56	0.33053	0.18201	0.59978	0.07100*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
O1	0.085 (4)	0.038 (3)	0.048 (3)	0.006 (2)	0.010 (3)	0.009 (2)
C2	0.045 (4)	0.046 (4)	0.045 (4)	−0.001 (3)	−0.000 (3)	0.012 (3)
O3	0.065 (4)	0.046 (3)	0.069 (4)	−0.004 (2)	0.016 (3)	0.009 (2)
C4	0.081 (6)	0.036 (4)	0.083 (6)	−0.006 (4)	0.013 (5)	0.010 (4)
C5	0.052 (5)	0.032 (3)	0.059 (5)	0.006 (3)	−0.004 (4)	0.005 (3)
C6	0.076 (6)	0.048 (4)	0.063 (5)	0.017 (4)	0.012 (4)	0.016 (4)
C21	0.042 (4)	0.036 (3)	0.043 (4)	−0.002 (3)	−0.004 (3)	0.005 (3)
C22	0.080 (6)	0.047 (4)	0.051 (5)	−0.010 (4)	0.002 (4)	0.006 (4)
C23	0.121 (9)	0.051 (5)	0.079 (7)	−0.021 (5)	−0.002 (6)	0.024 (5)
C24	0.099 (8)	0.047 (5)	0.080 (7)	0.009 (5)	−0.012 (6)	0.014 (4)
C25	0.080 (7)	0.058 (5)	0.079 (6)	0.011 (4)	0.013 (5)	0.014 (5)
C26	0.043 (4)	0.059 (5)	0.067 (5)	0.001 (3)	0.007 (4)	0.013 (4)
O5	0.064 (3)	0.033 (2)	0.059 (3)	0.006 (2)	−0.009 (3)	0.011 (2)
C50	0.045 (4)	0.047 (4)	0.043 (4)	0.004 (3)	−0.001 (3)	0.009 (3)
O50	0.078 (4)	0.040 (3)	0.061 (4)	0.004 (2)	−0.008 (3)	0.021 (2)
C51	0.051 (4)	0.034 (3)	0.056 (5)	0.003 (3)	0.004 (4)	0.015 (3)
C52	0.077 (6)	0.041 (4)	0.057 (5)	−0.001 (4)	−0.012 (4)	0.015 (3)
C53	0.087 (6)	0.041 (4)	0.063 (6)	0.002 (4)	−0.009 (5)	0.010 (4)
C54	0.061 (5)	0.039 (4)	0.068 (5)	0.003 (3)	0.009 (4)	0.021 (4)
Br54	0.1022 (8)	0.0383 (4)	0.1043 (8)	−0.0005 (4)	0.0082 (6)	0.0243 (4)
C55	0.091 (7)	0.053 (5)	0.060 (5)	0.011 (4)	0.001 (5)	0.028 (4)
C56	0.072 (6)	0.049 (4)	0.057 (5)	−0.005 (4)	−0.022 (4)	0.020 (4)

Geometric parameters (Å, º)

O1—C2	1.402 (9)	C24—C25	1.347 (15)
O1—C6	1.430 (9)	C24—H24	0.944
C2—O3	1.401 (9)	C25—C26	1.372 (12)
C2—C21	1.495 (9)	C25—H25	0.942
C2—H2	0.989	C26—H26	0.947
O3—C4	1.427 (9)	O5—C50	1.361 (8)
C4—C5	1.515 (12)	C50—O50	1.184 (11)
C4—H4a	0.944	C50—C51	1.496 (10)
C4—H4b	0.958	C51—C52	1.377 (9)
C5—C6	1.498 (11)	C51—C56	1.379 (13)
C5—O5	1.445 (8)	C52—C53	1.372 (11)
C5—H5	0.954	C52—H52	0.952
C6—H6a	0.949	C53—C54	1.376 (14)
C6—H6b	0.944	C53—H53	0.944
C21—C22	1.363 (12)	C54—Br54	1.890 (7)
C21—C26	1.383 (10)	C54—C55	1.377 (10)
C22—C23	1.393 (11)	C55—C56	1.372 (11)
C22—H22	0.962	C55—H55	0.938
C23—C24	1.381 (14)	C56—H56	0.948
C23—H23	0.947
C2—O1—C6	112.2 (6)	C22—C23—H23	119.6
O1—C2—O3	110.9 (5)	C24—C23—H23	120.5
O1—C2—C21	108.0 (7)	C23—C24—C25	119.4 (8)
O1—C2—H2	107.8	C23—C24—H24	119.1
O3—C2—C21	109.3 (5)	C25—C24—H24	121.4
O3—C2—H2	108.1	C24—C25—C26	120.4 (8)
C21—C2—H2	112.9	C24—C25—H25	119.2
C2—O3—C4	111.1 (6)	C26—C25—H25	120.3
O3—C4—C5	109.3 (8)	C21—C26—C25	121.7 (8)
O3—C4—H4a	110.8	C21—C26—H26	118.3
O3—C4—H4b	109.7	C25—C26—H26	119.9
C5—C4—H4a	109.5	C5—O5—C50	115.1 (6)
C5—C4—H4b	108.3	O5—C50—O50	123.7 (6)
H4a—C4—H4b	109.3	O5—C50—C51	111.6 (7)
C4—C5—C6	108.6 (6)	O50—C50—C51	124.7 (6)
C4—C5—O5	107.7 (7)	C50—C51—C52	117.9 (7)
C4—C5—H5	111.2	C50—C51—C56	122.9 (6)
C6—C5—O5	111.9 (6)	C52—C51—C56	119.2 (7)
C6—C5—H5	108.1	C51—C52—C53	120.9 (8)
O5—C5—H5	109.5	C51—C52—H52	117.9
O1—C6—C5	108.6 (6)	C53—C52—H52	121.2
O1—C6—H6a	109.6	C52—C53—C54	118.8 (7)
O1—C6—H6b	110.1	C52—C53—H53	120.7
C5—C6—H6a	109.1	C54—C53—H53	120.5
C5—C6—H6b	109.4	C53—C54—Br54	120.4 (5)
H6a—C6—H6b	110.1	C53—C54—C55	121.5 (7)
C2—C21—C22	121.2 (6)	Br54—C54—C55	118.1 (7)
C2—C21—C26	121.2 (7)	C54—C55—C56	118.7 (9)
C22—C21—C26	117.6 (6)	C54—C55—H55	120.4
C21—C22—C23	121.1 (8)	C56—C55—H55	120.8
C21—C22—H22	119.5	C51—C56—C55	120.9 (7)
C23—C22—H22	119.4	C51—C56—H56	119.7
C22—C23—C24	119.7 (10)	C55—C56—H56	119.4