1,4-Phenyl­ene diallyl bis­(carbonate)

The title mol­ecule, C₁₄H₁₄O₆, is based on a benzene core di-substituted by allyl carbonate groups in the para positions. The mol­ecule is placed on an inversion centre, and the substituents are twisted with respect to the central benzene ring plane. The crystal structure does not include significant inter­molecular inter­actions other than weak C—H...O contacts between CH groups in the benzene ring and carbonate O atoms.

Key indicators

Structure: I

• Single-crystal X-ray study
• T = 253 K
• Mean [sigma](C-C) = 0.002 Å
• R factor = 0.035
• wR factor = 0.102
• Data-to-parameter ratio = 16.5

checkCIF/PLATON results

No syntax errors found



Alert level C
PLAT905_ALERT_3_C Negative K value in the Analysis of Variance ...     -1.098 Report

Alert level G
PLAT802_ALERT_4_G CIF Input Record(s) with more than 80 Characters          3 Info
PLAT910_ALERT_3_G Missing # of FCF Reflection(s) Below Theta(Min).          1 Note
PLAT978_ALERT_2_G Number C-C Bonds with Positive Residual Density.          5 Info

   0 ALERT level A = Most likely a serious problem - resolve or explain
   0 ALERT level B = A potentially serious problem, consider carefully
   1 ALERT level C = Check. Ensure it is not caused by an omission or oversight
   3 ALERT level G = General information/check it is not something unexpected

   0 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
   2 ALERT type 3 Indicator that the structure quality may be low
   1 ALERT type 4 Improvement, methodology, query or suggestion
   0 ALERT type 5 Informative message, check

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Computing details

Data collection: X-AREA (Stoe & Cie, 2018); cell refinement: X-AREA (Stoe & Cie, 2018); data reduction: X-AREA (Stoe & Cie, 2018); program(s) used to solve structure: SHELXT2018/2 (Sheldrick, 2015a); program(s) used to refine structure: SHELXL2018/3 (Sheldrick, 2015b); molecular graphics: XP in SHELXTL-Plus (Sheldrick, 2008) and Mercury (Macrae et al., 2020); software used to prepare material for publication: publCIF (Westrip, 2010).

1,4-Phenylene diallyl bis(carbonate)

Crystal data

C14H14O6	F(000) = 292
Mr = 278.25	Dx = 1.328 Mg m^−3
Monoclinic, P21/n	Ag Kα radiation, λ = 0.56083 Å
a = 10.2808 (13) Å	Cell parameters from 19549 reflections
b = 5.4764 (6) Å	θ = 2.3–31.6°
c = 12.7396 (15) Å	µ = 0.06 mm^−1
β = 104.070 (9)°	T = 253 K
V = 695.74 (14) Å^3	Prism, colourless
Z = 2	0.60 × 0.50 × 0.50 mm

Data collection

Stoe Stadivari diffractometer	1620 independent reflections
Radiation source: Sealed X-ray tube, Axo Astix-f Microfocus source	1305 reflections with I > 2σ(I)
Graded multilayer mirror monochromator	Rint = 0.029
Detector resolution: 5.81 pixels mm^-1	θmax = 21.5°, θmin = 2.3°
ω scans	h = −13→13
Absorption correction: multi-scan (X-AREA; Stoe & Cie, 2018)	k = −7→7
Tmin = 0.536, Tmax = 1.000	l = −16→16
16744 measured reflections

Refinement

Refinement on F^2	Secondary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: mixed
R[F^2 > 2σ(F^2)] = 0.035	H atoms treated by a mixture of independent and constrained refinement
wR(F^2) = 0.102	w = 1/[σ^2(Fo^2) + (0.0441P)^2 + 0.1879P] where P = (Fo^2 + 2Fc^2)/3
S = 1.04	(Δ/σ)max < 0.001
1620 reflections	Δρmax = 0.18 e Å^−3
98 parameters	Δρmin = −0.15 e Å^−3
0 restraints	Extinction correction: SHELXL-2018/3 (Sheldrick 2015b), Fc^*=kFc[1+0.001xFc^2λ^3/sin(2θ)]^-1/4
0 constraints	Extinction coefficient: 0.023 (6)
Primary atom site location: dual

Special details

Refinement. Allyl H atoms (H10a and H10b) were refined with free coordinates, and other H atoms were placed on calculated positions. All H atoms were refined with isotropic displacements, calculated as U_iso(H) = 1.2×U_eq(carrier C atom).

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

	x	y	z	Uiso*/Ueq
C1	0.41290 (13)	0.3086 (2)	−0.03895 (10)	0.0404 (3)
H1	0.354051	0.182011	−0.066169	0.049*
C2	0.47808 (13)	0.3163 (2)	0.06961 (10)	0.0401 (3)
H2	0.464542	0.194551	0.116732	0.048*
C3	0.56326 (12)	0.5078 (2)	0.10622 (9)	0.0365 (3)
O4	0.63189 (9)	0.50484 (17)	0.21618 (7)	0.0450 (3)
C5	0.59396 (12)	0.6762 (2)	0.27902 (9)	0.0366 (3)
O6	0.51476 (10)	0.83464 (18)	0.24966 (7)	0.0498 (3)
O7	0.66007 (9)	0.63120 (18)	0.37984 (6)	0.0440 (3)
C8	0.62690 (13)	0.7968 (3)	0.45975 (10)	0.0444 (3)
H8A	0.532199	0.785459	0.457866	0.053*
H8B	0.646954	0.964013	0.444160	0.053*
C9	0.70837 (14)	0.7236 (3)	0.56723 (10)	0.0476 (3)
H9	0.799945	0.700847	0.575414	0.057*
C10	0.6593 (2)	0.6888 (3)	0.65149 (13)	0.0630 (4)
H10A	0.7141 (18)	0.644 (4)	0.7198 (16)	0.076*
H10B	0.5653 (19)	0.700 (4)	0.6461 (14)	0.076*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
C1	0.0448 (6)	0.0346 (6)	0.0399 (7)	−0.0038 (5)	0.0063 (5)	−0.0041 (5)
C2	0.0516 (7)	0.0331 (6)	0.0356 (6)	0.0008 (5)	0.0109 (5)	0.0029 (5)
C3	0.0409 (6)	0.0367 (6)	0.0290 (6)	0.0076 (5)	0.0031 (4)	−0.0027 (5)
O4	0.0532 (5)	0.0449 (5)	0.0309 (4)	0.0150 (4)	−0.0012 (4)	−0.0038 (4)
C5	0.0368 (6)	0.0387 (6)	0.0320 (6)	0.0025 (5)	0.0040 (4)	0.0004 (5)
O6	0.0567 (6)	0.0520 (6)	0.0366 (5)	0.0203 (4)	0.0035 (4)	0.0010 (4)
O7	0.0472 (5)	0.0508 (5)	0.0291 (4)	0.0135 (4)	0.0000 (3)	−0.0038 (4)
C8	0.0470 (7)	0.0497 (7)	0.0343 (6)	0.0064 (6)	0.0057 (5)	−0.0070 (5)
C9	0.0469 (7)	0.0544 (8)	0.0371 (7)	0.0016 (6)	0.0019 (5)	−0.0077 (6)
C10	0.0770 (11)	0.0669 (10)	0.0434 (8)	0.0006 (9)	0.0112 (7)	0.0051 (7)

Geometric parameters (Å, º)

C1—C3^i	1.3811 (17)	O7—C8	1.4640 (15)
C1—C2	1.3830 (17)	C8—C9	1.4763 (17)
C1—H1	0.9300	C8—H8A	0.9700
C2—C3	1.3733 (18)	C8—H8B	0.9700
C2—H2	0.9300	C9—C10	1.306 (2)
C3—O4	1.4071 (14)	C9—H9	0.9300
O4—C5	1.3513 (14)	C10—H10A	0.947 (19)
C5—O6	1.1863 (14)	C10—H10B	0.954 (18)
C5—O7	1.3221 (14)
C3^i—C1—C2	118.84 (11)	C5—O7—C8	114.10 (9)
C3^i—C1—H1	120.6	O7—C8—C9	107.53 (10)
C2—C1—H1	120.6	O7—C8—H8A	110.2
C3—C2—C1	118.48 (11)	C9—C8—H8A	110.2
C3—C2—H2	120.8	O7—C8—H8B	110.2
C1—C2—H2	120.8	C9—C8—H8B	110.2
C2—C3—C1^i	122.68 (11)	H8A—C8—H8B	108.5
C2—C3—O4	116.95 (11)	C10—C9—C8	123.81 (14)
C1^i—C3—O4	120.30 (11)	C10—C9—H9	118.1
C5—O4—C3	115.77 (9)	C8—C9—H9	118.1
O6—C5—O7	126.45 (11)	C9—C10—H10A	122.1 (12)
O6—C5—O4	126.58 (11)	C9—C10—H10B	121.3 (11)
O7—C5—O4	106.96 (9)	H10A—C10—H10B	116.6 (16)
C3^i—C1—C2—C3	0.5 (2)	C3—O4—C5—O7	174.50 (10)
C1—C2—C3—C1^i	−0.5 (2)	O6—C5—O7—C8	0.88 (19)
C1—C2—C3—O4	−177.58 (11)	O4—C5—O7—C8	−177.99 (10)
C2—C3—O4—C5	−110.62 (12)	C5—O7—C8—C9	−179.91 (11)
C1^i—C3—O4—C5	72.25 (15)	O7—C8—C9—C10	−130.59 (16)
C3—O4—C5—O6	−4.37 (19)

Symmetry code: (i) −x+1, −y+1, −z.

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
C1—H1···O7^ii	0.93	2.59	3.5100 (16)	169
C2—H2···O6^iii	0.93	2.57	3.4555 (16)	160

Symmetry codes: (ii) x−1/2, −y+1/2, z−1/2; (iii) x, y−1, z.