Crystal structure of the diglycidyl ether of eugenol

The diep­oxy monomer (DGE-Eu) was synthesized from eugenol by a three-step reaction. It consists of a 1,2,4-tris­ubstituted benzene ring substituted by diglycidyl ether, a meth­oxy group and a methyl­oxirane group. The three-membered oxirane rings are inclined to the benzene ring by 61.0 (3) and 27.9 (3)°. In the crystal, mol­ecules are linked by C—H...O hydrogen bonds, forming layers parallel to the ab plane.

Key indicators

• Single-crystal X-ray study
• T = 115 K
• Mean [sigma](C-C) = 0.004 Å
• Disorder in main residue
• R factor = 0.044
• wR factor = 0.121
• Data-to-parameter ratio = 16.8

checkCIF/PLATON results

No syntax errors found



Alert level C
DIFMX02_ALERT_1_C  The maximum difference density is > 0.1*ZMAX*0.75
            The relevant atom site should be identified.
PLAT094_ALERT_2_C Ratio of Maximum / Minimum Residual Density ....       2.45 Report
PLAT097_ALERT_2_C Large Reported Max.  (Positive) Residual Density       0.69 eA-3
PLAT220_ALERT_2_C Non-Solvent Resd 1   C   Ueq(max)/Ueq(min) Range        3.1 Ratio
PLAT340_ALERT_3_C Low Bond Precision on  C-C Bonds ...............    0.00433 Ang.

Alert level G
PLAT013_ALERT_1_G N.O.K. _shelx_hkl_checksum found in CIF ........     Please Check
PLAT301_ALERT_3_G Main Residue  Disorder ..............(Resd  1)..          6 % Note
PLAT398_ALERT_2_G Deviating  C-O-C  Angle from 120 Deg for O3            61.0 Degree
PLAT398_ALERT_2_G Deviating  C-O-C  Angle from 120 Deg for O4            60.2 Degree
PLAT792_ALERT_1_G The Model has Chirality at C8      (Polar  SPGR)          S Verify
PLAT978_ALERT_2_G Number C-C Bonds with Positive Residual Density.          7 Note

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

   3 ALERT type 1 CIF construction/syntax error, inconsistent or missing data
   6 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
   0 ALERT type 5 Informative message, check


checkCIF publication errors

Alert level A
PUBL024_ALERT_1_A The number of authors is greater than 5.
              Please specify the role of each of the co-authors
              for your paper.

   1 ALERT level A = Data missing that is essential or data in wrong format
   0 ALERT level G = General alerts. Data that may be required is missing

---

Computing details

Data collection: APEX2 (Bruker, 2014); cell refinement: SAINT (Bruker, 2014); data reduction: SAINT (Bruker, 2014); program(s) used to solve structure: SHELXT2015 (Sheldrick, 2015a); program(s) used to refine structure: SHELXL2015 (Sheldrick, 2015b); molecular graphics: OLEX2 (Dolomanov et al., 2009) and Mercury (Macrae et al., 2008); software used to prepare material for publication: OLEX2 (Dolomanov et al., 2009).

2-[3-Methoxy-4-(oxiran-2-ylmethoxy)benzyl]oxirane

Crystal data

C13H16O4	F(000) = 504
Mr = 236.26	Dx = 1.340 Mg m^−3
Monoclinic, Cc	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: C -2yc	Cell parameters from 9992 reflections
a = 9.8262 (5) Å	θ = 2.7–33.0°
b = 13.4434 (7) Å	µ = 0.10 mm^−1
c = 9.4251 (8) Å	T = 115 K
β = 109.897 (2)°	Prism, colourless
V = 1170.71 (13) Å^3	0.4 × 0.35 × 0.3 mm
Z = 4

Data collection

Bruker APEXII CCD diffractometer	2680 independent reflections
Radiation source: X-ray tube, Siemens KFF Mo 2K-180	2586 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.021
φ and ω scans	θmax = 27.5°, θmin = 2.7°
Absorption correction: multi-scan (SADABS; Bruker, 2014)	h = −12→12
Tmin = 0.700, Tmax = 0.747	k = −17→17
18897 measured reflections	l = −12→12

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)] = 0.044	H-atom parameters constrained
wR(F^2) = 0.121	w = 1/[σ^2(Fo^2) + (0.0641P)^2 + 1.3035P] where P = (Fo^2 + 2Fc^2)/3
S = 1.07	(Δ/σ)max < 0.001
2680 reflections	Δρmax = 0.69 e Å^−3
160 parameters	Δρmin = −0.28 e Å^−3
2 restraints	Absolute structure: Flack x determined using 1234 quotients [(I^+)-(I^-)]/[(I^+)+(I^-)] (Parsons et al., 2013)
Primary atom site location: structure-invariant direct methods	Absolute structure parameter: 0.20 (18)

Special details

Geometry. All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes.

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

	x	y	z	Uiso*/Ueq	Occ. (<1)
O1	0.3186 (2)	0.75130 (14)	0.4046 (2)	0.0215 (4)
O2	0.3043 (2)	0.59282 (15)	0.5548 (2)	0.0221 (4)
O3	0.0296 (3)	0.4884 (2)	0.5717 (4)	0.0511 (9)
O4	0.8644 (3)	0.79876 (18)	0.4484 (3)	0.0406 (7)
C1	0.6472 (3)	0.6219 (2)	0.3926 (3)	0.0204 (6)
C2	0.6394 (3)	0.5387 (2)	0.4744 (3)	0.0203 (5)
H2	0.7121	0.4890	0.4925	0.024*
C3	0.5262 (3)	0.5260 (2)	0.5313 (3)	0.0204 (6)
H3	0.5220	0.4677	0.5867	0.025*
C4	0.4203 (3)	0.5984 (2)	0.5068 (3)	0.0169 (5)
C5	0.4272 (3)	0.6842 (2)	0.4242 (3)	0.0171 (5)
C6	0.5397 (3)	0.6949 (2)	0.3680 (3)	0.0187 (5)
H6	0.5441	0.7527	0.3119	0.022*
C7	0.2935 (3)	0.5033 (3)	0.6333 (4)	0.0287 (7)
H7A	0.3828	0.4935	0.7213	0.034*
H7B	0.2807	0.4452	0.5655	0.034*
C8	0.1678 (4)	0.5132 (3)	0.6838 (5)	0.0382 (8)
H8	0.1691	0.5701	0.7526	0.046*
C9	0.0890 (4)	0.4237 (4)	0.6998 (5)	0.0522 (12)
H9A	0.1274	0.3584	0.6826	0.063*
H9B	0.0428	0.4238	0.7782	0.063*
C10	0.3084 (3)	0.8287 (2)	0.2985 (4)	0.0269 (6)
H10A	0.3053	0.7997	0.2020	0.040*
H10B	0.3929	0.8724	0.3366	0.040*
H10C	0.2201	0.8674	0.2839	0.040*
C11	0.7701 (3)	0.6367 (3)	0.3324 (4)	0.0278 (7)
H11A	0.8071	0.5708	0.3159	0.033*	0.690 (11)
H11B	0.7323	0.6706	0.2334	0.033*	0.690 (11)
H11C	0.8536	0.5974	0.3965	0.033*	0.310 (11)
H11D	0.7401	0.6074	0.2299	0.033*	0.310 (11)
C13	0.9712 (4)	0.7691 (2)	0.3826 (4)	0.0324 (7)
H13A	0.9471	0.7781	0.2725	0.039*	0.690 (11)
H13B	1.0745	0.7788	0.4434	0.039*	0.690 (11)
H13C	1.0477	0.7222	0.4401	0.039*	0.310 (11)
H13D	1.0014	0.8187	0.3216	0.039*	0.310 (11)
C12A	0.8911 (4)	0.6954 (3)	0.4331 (5)	0.0203 (11)	0.690 (11)
H12A	0.9476	0.6614	0.5295	0.024*	0.690 (11)
C12B	0.8184 (12)	0.7317 (8)	0.3230 (12)	0.032 (3)*	0.310 (11)
H12B	0.7600	0.7658	0.2274	0.038*	0.310 (11)

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
O1	0.0200 (9)	0.0204 (9)	0.0264 (10)	0.0043 (7)	0.0107 (7)	0.0072 (8)
O2	0.0216 (10)	0.0238 (10)	0.0222 (9)	−0.0004 (8)	0.0089 (8)	0.0056 (8)
O3	0.0229 (12)	0.0500 (17)	0.070 (2)	−0.0009 (11)	0.0028 (12)	0.0306 (16)
O4	0.0437 (14)	0.0246 (12)	0.0679 (18)	−0.0074 (10)	0.0379 (13)	−0.0174 (12)
C1	0.0174 (12)	0.0230 (13)	0.0210 (13)	−0.0033 (11)	0.0067 (10)	−0.0078 (11)
C2	0.0186 (12)	0.0202 (12)	0.0194 (12)	0.0029 (10)	0.0029 (10)	−0.0036 (10)
C3	0.0226 (13)	0.0187 (12)	0.0168 (12)	−0.0001 (10)	0.0026 (10)	0.0014 (9)
C4	0.0165 (12)	0.0195 (13)	0.0129 (11)	−0.0036 (9)	0.0026 (10)	0.0003 (9)
C5	0.0160 (11)	0.0170 (12)	0.0167 (11)	0.0005 (9)	0.0035 (9)	−0.0010 (9)
C6	0.0191 (12)	0.0175 (12)	0.0198 (12)	−0.0019 (9)	0.0068 (10)	−0.0008 (9)
C7	0.0218 (14)	0.0326 (16)	0.0299 (15)	0.0008 (12)	0.0067 (11)	0.0146 (13)
C8	0.0330 (17)	0.042 (2)	0.0429 (19)	0.0016 (15)	0.0170 (15)	0.0098 (16)
C9	0.0247 (16)	0.056 (2)	0.075 (3)	0.0001 (16)	0.0159 (18)	0.040 (2)
C10	0.0292 (15)	0.0234 (14)	0.0304 (15)	0.0051 (12)	0.0133 (12)	0.0108 (12)
C11	0.0215 (13)	0.0314 (16)	0.0346 (16)	−0.0047 (12)	0.0146 (12)	−0.0140 (12)
C13	0.0323 (16)	0.0259 (14)	0.049 (2)	−0.0044 (13)	0.0267 (15)	−0.0069 (14)
C12A	0.021 (2)	0.020 (2)	0.023 (2)	0.0008 (15)	0.0118 (16)	−0.0013 (15)

Geometric parameters (Å, º)

O1—C5	1.361 (3)	C8—H8	1.0000
O1—C10	1.423 (3)	C8—C9	1.467 (5)
O2—C4	1.364 (3)	C9—H9A	0.9900
O2—C7	1.435 (3)	C9—H9B	0.9900
O3—C8	1.447 (5)	C10—H10A	0.9800
O3—C9	1.441 (4)	C10—H10B	0.9800
O4—C13	1.444 (4)	C10—H10C	0.9800
O4—C12A	1.430 (4)	C11—H11A	0.9900
O4—C12B	1.432 (11)	C11—H11B	0.9900
C1—C2	1.374 (4)	C11—H11C	0.9900
C1—C6	1.402 (4)	C11—H11D	0.9900
C1—C11	1.513 (4)	C11—C12A	1.473 (5)
C2—H2	0.9500	C11—C12B	1.375 (12)
C2—C3	1.400 (4)	C13—H13A	0.9900
C3—H3	0.9500	C13—H13B	0.9900
C3—C4	1.386 (4)	C13—H13C	0.9900
C4—C5	1.406 (4)	C13—H13D	0.9900
C5—C6	1.386 (4)	C13—C12A	1.443 (5)
C6—H6	0.9500	C13—C12B	1.499 (12)
C7—H7A	0.9900	C12A—H12A	1.0000
C7—H7B	0.9900	C12B—H12B	1.0000
C7—C8	1.473 (5)
C5—O1—C10	116.4 (2)	O1—C10—H10B	109.5
C4—O2—C7	115.7 (2)	O1—C10—H10C	109.5
C9—O3—C8	61.1 (2)	H10A—C10—H10B	109.5
C12A—O4—C13	60.3 (2)	H10A—C10—H10C	109.5
C12B—O4—C13	62.8 (5)	H10B—C10—H10C	109.5
C2—C1—C6	118.7 (3)	C1—C11—H11A	108.8
C2—C1—C11	121.4 (3)	C1—C11—H11B	108.8
C6—C1—C11	119.9 (3)	C1—C11—H11C	107.6
C1—C2—H2	119.4	C1—C11—H11D	107.6
C1—C2—C3	121.1 (3)	H11A—C11—H11B	107.7
C3—C2—H2	119.4	H11C—C11—H11D	107.0
C2—C3—H3	120.0	C12A—C11—C1	113.6 (3)
C4—C3—C2	120.0 (2)	C12A—C11—H11A	108.8
C4—C3—H3	120.0	C12A—C11—H11B	108.8
O2—C4—C3	124.8 (2)	C12B—C11—C1	118.9 (5)
O2—C4—C5	115.6 (2)	C12B—C11—H11C	107.6
C3—C4—C5	119.6 (2)	C12B—C11—H11D	107.6
O1—C5—C4	115.8 (2)	O4—C13—H13A	117.8
O1—C5—C6	124.7 (2)	O4—C13—H13B	117.8
C6—C5—C4	119.5 (2)	O4—C13—H13C	118.0
C1—C6—H6	119.4	O4—C13—H13D	118.0
C5—C6—C1	121.2 (2)	O4—C13—C12B	58.2 (5)
C5—C6—H6	119.4	H13A—C13—H13B	115.0
O2—C7—H7A	110.1	H13C—C13—H13D	115.1
O2—C7—H7B	110.1	C12A—C13—O4	59.4 (2)
O2—C7—C8	108.0 (3)	C12A—C13—H13A	117.8
H7A—C7—H7B	108.4	C12A—C13—H13B	117.8
C8—C7—H7A	110.1	C12B—C13—H13C	118.0
C8—C7—H7B	110.1	C12B—C13—H13D	118.0
O3—C8—C7	115.2 (3)	O4—C12A—C11	116.8 (3)
O3—C8—H8	116.8	O4—C12A—C13	60.4 (2)
O3—C8—C9	59.3 (2)	O4—C12A—H12A	114.7
C7—C8—H8	116.8	C11—C12A—H12A	114.7
C9—C8—C7	119.3 (4)	C13—C12A—C11	124.5 (4)
C9—C8—H8	116.8	C13—C12A—H12A	114.7
O3—C9—C8	59.7 (2)	O4—C12B—C13	59.0 (5)
O3—C9—H9A	117.8	O4—C12B—H12B	112.2
O3—C9—H9B	117.8	C11—C12B—O4	123.4 (8)
C8—C9—H9A	117.8	C11—C12B—C13	127.6 (8)
C8—C9—H9B	117.8	C11—C12B—H12B	112.2
H9A—C9—H9B	114.9	C13—C12B—H12B	112.2
O1—C10—H10A	109.5
O1—C5—C6—C1	−179.6 (3)	C3—C4—C5—O1	179.6 (2)
O2—C4—C5—O1	0.9 (3)	C3—C4—C5—C6	0.2 (4)
O2—C4—C5—C6	−178.5 (2)	C4—O2—C7—C8	176.7 (3)
O2—C7—C8—O3	83.5 (4)	C4—C5—C6—C1	−0.2 (4)
O2—C7—C8—C9	150.9 (4)	C6—C1—C2—C3	0.6 (4)
O4—C13—C12A—C11	103.8 (4)	C6—C1—C11—C12A	84.8 (4)
O4—C13—C12B—C11	−110.4 (10)	C6—C1—C11—C12B	31.8 (7)
C1—C2—C3—C4	−0.7 (4)	C7—O2—C4—C3	−1.3 (4)
C1—C11—C12A—O4	−69.5 (4)	C7—O2—C4—C5	177.3 (2)
C1—C11—C12A—C13	−140.5 (3)	C7—C8—C9—O3	−103.5 (4)
C1—C11—C12B—O4	54.5 (11)	C9—O3—C8—C7	110.4 (4)
C1—C11—C12B—C13	128.8 (8)	C10—O1—C5—C4	−168.6 (2)
C2—C1—C6—C5	−0.1 (4)	C10—O1—C5—C6	10.8 (4)
C2—C1—C11—C12A	−93.8 (4)	C11—C1—C2—C3	179.3 (2)
C2—C1—C11—C12B	−146.8 (6)	C11—C1—C6—C5	−178.8 (2)
C2—C3—C4—O2	178.8 (2)	C13—O4—C12A—C11	−116.3 (4)
C2—C3—C4—C5	0.3 (4)	C13—O4—C12B—C11	117.2 (10)

Hydrogen-bond geometry (Å, º)

Cg is the centroid of the benzene ring (C1–C6).

D—H···A	D—H	H···A	D···A	D—H···A
C7—H7B···O4^i	0.99	2.53	3.452 (4)	155
C11—H11C···O3^ii	0.99	2.43	3.413 (4)	170
C13—H13B···O1^ii	0.99	2.57	3.358 (4)	136
C12A—H12A···O3^ii	1.00	2.45	3.177 (5)	129
C7—H7A···Cg^iii	0.99	2.57	3.465 (4)	150

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