Crystal structure of the monoglycidyl ether of isoeugenol

The crystal structure of the trans isomer of monoglycidyl ether of iso-eugenol [GE-isoEu; systematic name 2-({2-meth­oxy-4-[(E)-1-propen-1-yl]phen­oxy}meth­yl)oxirane] was determined. From a supra­molecular point of view, mol­ecules of GE-isoEu are stacked through offset π-stacking inter­actions involving the aromatic rings.

Key indicators

• Single-crystal X-ray study
• T = 150 K
• Mean [sigma](C-C) = 0.003 Å
• R factor = 0.049
• wR factor = 0.128
• Data-to-parameter ratio = 18.0

checkCIF/PLATON results

No syntax errors found



Alert level C
PLAT911_ALERT_3_C Missing FCF Refl Between Thmin & STh/L=    0.600          4 Report

Alert level G
PLAT398_ALERT_2_G Deviating  C-O-C   Angle From 120 for O1       .       60.7 Degree
PLAT793_ALERT_4_G Model has Chirality at C2          (Centro SPGR)          S Verify
PLAT910_ALERT_3_G Missing # of FCF Reflection(s) Below Theta(Min).          1 Note
PLAT912_ALERT_4_G Missing # of FCF Reflections Above STh/L=  0.600          2 Note
PLAT933_ALERT_2_G Number of HKL-OMIT Records in Embedded .res File          4 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
   6 ALERT level G = General information/check it is not something unexpected

   0 ALERT type 1 CIF construction/syntax error, inconsistent or missing data
   3 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
   2 ALERT type 4 Improvement, methodology, query or suggestion
   0 ALERT type 5 Informative message, check

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Computing details

Data collection: APEX3 (Bruker, 2020); cell refinement: SAINT (Bruker, 2016); data reduction: SAINT (Bruker, 2016); program(s) used to solve structure: SHELXT2014/5 (Sheldrick, 2015a); program(s) used to refine structure: SHELXL2018/3 (Sheldrick, 2015b); molecular graphics: OLEX2 (Dolomanov et al., 2009); software used to prepare material for publication: OLEX2 (Dolomanov et al., 2009).

2-[2-Methoxy-4-(prop-1-en-1-yl)phenoxymethyl]oxirane

Crystal data

C13H16O3	Z = 2
Mr = 220.26	F(000) = 236
Triclinic, P1	Dx = 1.259 Mg m^−3
a = 4.5931 (5) Å	Mo Kα radiation, λ = 0.71073 Å
b = 8.9134 (9) Å	Cell parameters from 5145 reflections
c = 15.0764 (18) Å	θ = 2.5–26.6°
α = 74.808 (3)°	µ = 0.09 mm^−1
β = 85.309 (4)°	T = 150 K
γ = 77.430 (3)°	PRISM, colourless
V = 581.18 (11) Å^3	0.5 × 0.15 × 0.15 mm

Data collection

Bruker kappa APEXII diffractometer	2647 independent reflections
Radiation source: X-ray tube, Siemens KFF Mo 2K-180	1865 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.038
Detector resolution: 8.3 pixels mm^-1	θmax = 27.5°, θmin = 2.4°
φ and ω scans	h = −5→5
Absorption correction: multi-scan (SADABS; Krause et al., 2015)	k = −11→11
Tmin = 0.668, Tmax = 0.746	l = −19→19
17290 measured reflections

Refinement

Refinement on F^2	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F^2 > 2σ(F^2)] = 0.049	Hydrogen site location: inferred from neighbouring sites
wR(F^2) = 0.128	H-atom parameters constrained
S = 1.03	w = 1/[σ^2(Fo^2) + (0.0417P)^2 + 0.3763P] where P = (Fo^2 + 2Fc^2)/3
2647 reflections	(Δ/σ)max < 0.001
147 parameters	Δρmax = 0.33 e Å^−3
0 restraints	Δρmin = −0.19 e Å^−3

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
O3	0.5215 (3)	0.37762 (14)	0.60436 (8)	0.0300 (3)
O2	0.8022 (3)	0.53432 (15)	0.67363 (9)	0.0327 (3)
O1	0.7925 (3)	0.88375 (17)	0.59690 (12)	0.0498 (4)
C5	0.6121 (4)	0.3053 (2)	0.69197 (11)	0.0234 (4)
C6	0.5628 (4)	0.1597 (2)	0.74236 (12)	0.0262 (4)
H6	0.457467	0.102195	0.715929	0.031*
C4	0.7670 (4)	0.3919 (2)	0.73067 (12)	0.0247 (4)
C7	0.6660 (4)	0.0952 (2)	0.83221 (12)	0.0307 (4)
C9	0.8683 (4)	0.3293 (2)	0.81886 (13)	0.0322 (4)
H9	0.973015	0.386713	0.845569	0.039*
C3	0.9823 (4)	0.6233 (2)	0.70261 (14)	0.0319 (4)
H3A	1.174343	0.554383	0.725793	0.038*
H3B	0.878503	0.670214	0.752225	0.038*
C8	0.8175 (4)	0.1822 (2)	0.86875 (13)	0.0356 (5)
H8	0.888622	0.140217	0.929532	0.043*
C10	0.3618 (4)	0.2968 (2)	0.56109 (12)	0.0288 (4)
H10A	0.312228	0.360518	0.498608	0.043*
H10B	0.177676	0.280713	0.596581	0.043*
H10C	0.485826	0.193544	0.558386	0.043*
C11	0.6167 (5)	−0.0610 (2)	0.88692 (13)	0.0393 (5)
H11	0.697432	−0.096779	0.946634	0.047*
C2	1.0334 (4)	0.7498 (2)	0.62068 (15)	0.0376 (5)
H2	1.143379	0.712477	0.567846	0.045*
C12	0.4742 (5)	−0.1566 (2)	0.86288 (15)	0.0462 (6)
H12	0.392242	−0.122483	0.803335	0.055*
C1	1.0655 (5)	0.9043 (2)	0.62760 (18)	0.0450 (5)
H1A	1.065235	0.921634	0.689846	0.054*
H1B	1.195933	0.961206	0.581395	0.054*
C13	0.4301 (6)	−0.3142 (3)	0.92108 (17)	0.0583 (7)
H13A	0.509844	−0.396339	0.888173	0.087*
H13B	0.216596	−0.310609	0.934385	0.087*
H13C	0.534885	−0.338975	0.978846	0.087*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
O3	0.0366 (7)	0.0279 (7)	0.0274 (6)	−0.0150 (5)	−0.0068 (5)	−0.0015 (5)
O2	0.0337 (7)	0.0320 (7)	0.0361 (7)	−0.0159 (5)	−0.0066 (6)	−0.0057 (6)
O1	0.0354 (8)	0.0392 (9)	0.0766 (11)	−0.0119 (7)	−0.0132 (7)	−0.0106 (8)
C5	0.0197 (8)	0.0257 (9)	0.0231 (8)	−0.0015 (7)	0.0001 (6)	−0.0060 (7)
C6	0.0266 (9)	0.0240 (9)	0.0268 (9)	−0.0029 (7)	0.0019 (7)	−0.0068 (7)
C4	0.0185 (8)	0.0255 (9)	0.0290 (9)	−0.0020 (7)	0.0002 (7)	−0.0071 (7)
C7	0.0323 (10)	0.0251 (9)	0.0276 (9)	0.0058 (7)	0.0037 (7)	−0.0052 (7)
C9	0.0275 (9)	0.0362 (11)	0.0331 (10)	−0.0001 (8)	−0.0045 (8)	−0.0130 (8)
C3	0.0215 (9)	0.0350 (10)	0.0444 (11)	−0.0065 (7)	−0.0044 (8)	−0.0175 (9)
C8	0.0390 (11)	0.0352 (11)	0.0259 (9)	0.0063 (8)	−0.0046 (8)	−0.0064 (8)
C10	0.0315 (9)	0.0293 (10)	0.0288 (9)	−0.0132 (7)	−0.0015 (7)	−0.0070 (7)
C11	0.0492 (12)	0.0295 (11)	0.0281 (10)	0.0056 (9)	0.0039 (9)	−0.0005 (8)
C2	0.0257 (10)	0.0380 (11)	0.0545 (13)	−0.0114 (8)	0.0037 (9)	−0.0188 (10)
C12	0.0630 (15)	0.0281 (11)	0.0378 (12)	−0.0021 (10)	0.0079 (10)	−0.0001 (9)
C1	0.0323 (11)	0.0379 (12)	0.0731 (16)	−0.0144 (9)	−0.0054 (10)	−0.0211 (11)
C13	0.0827 (18)	0.0276 (12)	0.0526 (14)	−0.0028 (11)	0.0208 (13)	−0.0029 (10)

Geometric parameters (Å, º)

O3—C5	1.364 (2)	C3—C2	1.479 (3)
O3—C10	1.427 (2)	C8—H8	0.9500
O2—C4	1.368 (2)	C10—H10A	0.9800
O2—C3	1.425 (2)	C10—H10B	0.9800
O1—C2	1.430 (2)	C10—H10C	0.9800
O1—C1	1.435 (2)	C11—H11	0.9500
C5—C6	1.377 (2)	C11—C12	1.315 (3)
C5—C4	1.408 (2)	C2—H2	1.0000
C6—H6	0.9500	C2—C1	1.448 (3)
C6—C7	1.403 (2)	C12—H12	0.9500
C4—C9	1.377 (2)	C12—C13	1.495 (3)
C7—C8	1.382 (3)	C1—H1A	0.9900
C7—C11	1.474 (3)	C1—H1B	0.9900
C9—H9	0.9500	C13—H13A	0.9800
C9—C8	1.388 (3)	C13—H13B	0.9800
C3—H3A	0.9900	C13—H13C	0.9800
C3—H3B	0.9900
C5—O3—C10	117.72 (13)	O3—C10—H10C	109.5
C4—O2—C3	118.70 (14)	H10A—C10—H10B	109.5
C2—O1—C1	60.72 (12)	H10A—C10—H10C	109.5
O3—C5—C6	125.24 (15)	H10B—C10—H10C	109.5
O3—C5—C4	114.77 (15)	C7—C11—H11	116.1
C6—C5—C4	119.99 (16)	C12—C11—C7	127.7 (2)
C5—C6—H6	119.5	C12—C11—H11	116.1
C5—C6—C7	120.90 (17)	O1—C2—C3	116.11 (16)
C7—C6—H6	119.5	O1—C2—H2	115.7
O2—C4—C5	114.35 (15)	O1—C2—C1	59.82 (12)
O2—C4—C9	126.27 (16)	C3—C2—H2	115.7
C9—C4—C5	119.38 (16)	C1—C2—C3	122.05 (19)
C6—C7—C11	121.60 (18)	C1—C2—H2	115.7
C8—C7—C6	118.10 (17)	C11—C12—H12	117.2
C8—C7—C11	120.29 (17)	C11—C12—C13	125.7 (2)
C4—C9—H9	120.0	C13—C12—H12	117.2
C4—C9—C8	119.97 (18)	O1—C1—C2	59.46 (12)
C8—C9—H9	120.0	O1—C1—H1A	117.8
O2—C3—H3A	110.5	O1—C1—H1B	117.8
O2—C3—H3B	110.5	C2—C1—H1A	117.8
O2—C3—C2	106.23 (15)	C2—C1—H1B	117.8
H3A—C3—H3B	108.7	H1A—C1—H1B	115.0
C2—C3—H3A	110.5	C12—C13—H13A	109.5
C2—C3—H3B	110.5	C12—C13—H13B	109.5
C7—C8—C9	121.65 (17)	C12—C13—H13C	109.5
C7—C8—H8	119.2	H13A—C13—H13B	109.5
C9—C8—H8	119.2	H13A—C13—H13C	109.5
O3—C10—H10A	109.5	H13B—C13—H13C	109.5
O3—C10—H10B	109.5
O3—C5—C6—C7	179.86 (15)	C4—O2—C3—C2	167.73 (14)
O3—C5—C4—O2	−0.3 (2)	C4—C5—C6—C7	−0.3 (2)
O3—C5—C4—C9	−179.96 (15)	C4—C9—C8—C7	0.0 (3)
O2—C4—C9—C8	−179.64 (16)	C7—C11—C12—C13	−179.97 (19)
O2—C3—C2—O1	78.43 (19)	C3—O2—C4—C5	−173.56 (14)
O2—C3—C2—C1	147.72 (17)	C3—O2—C4—C9	6.1 (2)
C5—C6—C7—C8	0.2 (2)	C3—C2—C1—O1	−103.7 (2)
C5—C6—C7—C11	−179.63 (16)	C8—C7—C11—C12	178.9 (2)
C5—C4—C9—C8	0.0 (3)	C10—O3—C5—C6	0.2 (2)
C6—C5—C4—O2	179.83 (14)	C10—O3—C5—C4	−179.68 (14)
C6—C5—C4—C9	0.2 (2)	C11—C7—C8—C9	179.78 (17)
C6—C7—C8—C9	−0.1 (3)	C1—O1—C2—C3	113.5 (2)
C6—C7—C11—C12	−1.2 (3)