1-(Methyl-α-D-gluco­pyran­osid-6-yl)-3-vinyl­imidazolium iodide di­methyl­formamide monosolvate

The title solvated molecular salt, [MeGluVIm]I (MeGluVIm = 1-(methyl-α-D-gluco­pyran­osid-6-yl)-3-vinyl­imidazolium), or C₁₂H₁₉N₂O₅⁺·I⁻·C₃H₇NO, was synthesized from methyl-α-D-6-iodo­gluco­pyran­oside and vinyl­imidazole in DMF. It crystallizes through precipitation from ethyl acetate solution directly after the reaction procedure. The crystal structure consists of an iodide anion and a [MeGluVIm] cation. Furthermore, the crystal structure contains one mol­ecule of DMF, which accepts two O—H...H hydrogen bonds from the OH groups of the gluco­pyran­oside.

Key indicators

• Single-crystal X-ray study
• T = 123 K
• Mean [sigma](C-C) = 0.005 Å
• R factor = 0.028
• wR factor = 0.060
• Data-to-parameter ratio = 25.1

checkCIF/PLATON results

No syntax errors found



Alert level C
PLAT094_ALERT_2_C Ratio of Maximum / Minimum Residual Density ....       3.24 Report
PLAT414_ALERT_2_C Short Intra D-H..H-X       H2       ..H3A      .       1.99 Ang.
                                                      x,y,z  =      1_555 Check
PLAT910_ALERT_3_C Missing # of FCF Reflection(s) Below Theta(Min).          9 Note

Alert level G
PLAT042_ALERT_1_G Calc. and Reported Moiety Formula Strings Differ     Please Check
PLAT790_ALERT_4_G Centre of Gravity not Within Unit Cell: Resd.  #          3 Note
              I
PLAT791_ALERT_4_G Model has Chirality at C1          (Sohnke SpGr)          S Verify
PLAT791_ALERT_4_G Model has Chirality at C2          (Sohnke SpGr)          R Verify
PLAT791_ALERT_4_G Model has Chirality at C3          (Sohnke SpGr)          S Verify
PLAT791_ALERT_4_G Model has Chirality at C4          (Sohnke SpGr)          S Verify
PLAT791_ALERT_4_G Model has Chirality at C5          (Sohnke SpGr)          R Verify
PLAT933_ALERT_2_G Number of HKL-OMIT Records in Embedded .res File          8 Note
PLAT978_ALERT_2_G Number C-C Bonds with Positive Residual Density.          4 Info

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

   1 ALERT type 1 CIF construction/syntax error, inconsistent or missing data
   4 ALERT type 2 Indicator that the structure model may be wrong or deficient
   1 ALERT type 3 Indicator that the structure quality may be low
   6 ALERT type 4 Improvement, methodology, query or suggestion
   0 ALERT type 5 Informative message, check

---

Computing details

Data collection: APEX2 (Bruker, 2003); cell refinement: SAINT (Bruker, 2003); data reduction: SAINT (Bruker, 2003); program(s) used to solve structure: SHELXTL (Sheldrick, 2008); program(s) used to refine structure: SHELXL2014/7 (Sheldrick, 2015); molecular graphics: ORTEP-3 for Windows (Farrugia, 2012); software used to prepare material for publication: SHELXL2014/7 (Sheldrick, 2015).

3-Ethenyl-1-(methyl-α-D-glucopyranosid-6-yl)imidazolium iodide dimethylformamide monosolvate

Crystal data

C12H19N2O5^+·I^−·C3H7NO	F(000) = 476
Mr = 471.29	Dx = 1.638 Mg m^−3
Monoclinic, P21	Mo Kα radiation, λ = 0.71073 Å
a = 10.816 (2) Å	Cell parameters from 7185 reflections
b = 7.0106 (15) Å	θ = 3.2–31.1°
c = 13.169 (3) Å	µ = 1.71 mm^−1
β = 106.833 (4)°	T = 123 K
V = 955.7 (3) Å^3	Needle, colourless
Z = 2	0.29 × 0.08 × 0.03 mm

Data collection

Bruker Kappa APEXII CCD diffractometer	6072 independent reflections
Radiation source: sealed tube	5626 reflections with I > 2σ(I)
Detector resolution: 10.4167 pixels mm^-1	Rint = 0.038
phi and ω scans	θmax = 31.0°, θmin = 3.8°
Absorption correction: multi-scan (SADABS; Bruker, 2003)	h = −15→15
Tmin = 0.629, Tmax = 0.746	k = −10→10
17430 measured reflections	l = −19→18

Refinement

Refinement on F^2	Hydrogen site location: mixed
Least-squares matrix: full	H atoms treated by a mixture of independent and constrained refinement
R[F^2 > 2σ(F^2)] = 0.028	w = 1/[σ^2(Fo^2) + (0.0231P)^2] where P = (Fo^2 + 2Fc^2)/3
wR(F^2) = 0.060	(Δ/σ)max = 0.001
S = 1.03	Δρmax = 1.42 e Å^−3
6072 reflections	Δρmin = −0.44 e Å^−3
242 parameters	Absolute structure: Refined as an inversion twin, 2815 Friedel pairs.
1 restraint	Absolute structure parameter: 0.006 (19)

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.

Refinement. All H atoms were positioned geometrically and refined using a riding model, with C—H = 0.98 (methyl groups), 0.99Å (methylene groups), 1.00Å (methine groups) or 0.95 Å (aryl CH) and with U_iso(H) = 1.5 times U_eq(C) (methyl groups) or with U_iso(H) = 1.2 times U_eq(C) (methylene groups, aryl CH, methine groups). Torsion angles of all methyl groups were allowed to refine.

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 > 2σ(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.

Refined as a two-component inversion twin.

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

	x	y	z	Uiso*/Ueq
N1	0.1863 (3)	1.0859 (4)	0.3364 (2)	0.0151 (5)
N2	0.1065 (3)	1.1296 (4)	0.1676 (2)	0.0179 (6)
O1	0.3511 (2)	0.8245 (4)	0.4934 (2)	0.0146 (5)
O2	0.3182 (3)	0.5032 (4)	0.4445 (2)	0.0184 (5)
O3	0.4060 (3)	0.3939 (4)	0.6541 (3)	0.0222 (6)
O4	0.2120 (3)	0.5948 (4)	0.7282 (2)	0.0197 (5)
O5	0.0572 (2)	0.8579 (4)	0.5786 (2)	0.0169 (5)
C1	0.3882 (3)	0.6322 (5)	0.5202 (3)	0.0150 (7)
H1	0.4821	0.6180	0.5263	0.018*
C2	0.3673 (3)	0.5847 (5)	0.6269 (3)	0.0156 (6)
H2	0.4240	0.6703	0.6816	0.019*
C3	0.2266 (3)	0.6217 (5)	0.6246 (3)	0.0137 (6)
H3	0.1679	0.5327	0.5733	0.016*
C4	0.1910 (3)	0.8273 (5)	0.5914 (3)	0.0129 (6)
H4	0.2438	0.9163	0.6464	0.015*
C5	0.2174 (3)	0.8639 (4)	0.4853 (3)	0.0123 (6)
H5	0.1607	0.7793	0.4299	0.015*
C6	0.1951 (3)	1.0688 (4)	0.4498 (3)	0.0139 (6)
H6A	0.1141	1.1156	0.4618	0.017*
H6B	0.2671	1.1487	0.4921	0.017*
C7	0.3439 (4)	0.5229 (5)	0.3446 (3)	0.0238 (8)
H7A	0.3086	0.4128	0.2997	0.036*
H7B	0.4374	0.5295	0.3558	0.036*
H7C	0.3033	0.6400	0.3097	0.036*
C8	0.0831 (3)	1.1454 (4)	0.2617 (3)	0.0153 (7)
H8	0.0055	1.1915	0.2729	0.018*
C9	0.2788 (3)	1.0274 (5)	0.2893 (3)	0.0174 (7)
H9	0.3618	0.9775	0.3244	0.021*
C10	0.2286 (4)	1.0547 (5)	0.1843 (3)	0.0200 (7)
H10	0.2698	1.0273	0.1313	0.024*
C11	0.0197 (3)	1.1684 (9)	0.0656 (3)	0.0238 (7)
H11	0.0524	1.1636	0.0060	0.029*
C12	−0.1014 (4)	1.2099 (7)	0.0494 (3)	0.0322 (11)
H12A	−0.1368	1.2158	0.1075	0.039*
H12B	−0.1547	1.2344	−0.0205	0.039*
H3A	0.426 (4)	0.391 (7)	0.711 (3)	0.014 (12)*
H4A	0.186 (4)	0.495 (7)	0.740 (4)	0.025 (12)*
H5A	0.051 (4)	0.940 (7)	0.612 (4)	0.018 (12)*
I1	0.06251 (2)	1.18116 (3)	0.77975 (2)	0.02003 (6)
N3	0.4772 (3)	0.4326 (5)	1.0319 (3)	0.0235 (7)
O7	0.5214 (3)	0.4185 (5)	0.8731 (2)	0.0306 (7)
C13	0.6115 (5)	0.4439 (8)	1.0952 (4)	0.0328 (10)
H13A	0.6663	0.4637	1.0485	0.049*
H13B	0.6363	0.3249	1.1349	0.049*
H13C	0.6225	0.5508	1.1450	0.049*
C14	0.3817 (4)	0.4304 (7)	1.0890 (4)	0.0341 (10)
H14A	0.3828	0.5529	1.1250	0.051*
H14B	0.4016	0.3275	1.1416	0.051*
H14C	0.2960	0.4092	1.0391	0.051*
C15	0.4445 (5)	0.4205 (6)	0.9273 (4)	0.0241 (8)
H15	0.3550	0.4126	0.8906	0.029*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
N1	0.0161 (13)	0.0129 (12)	0.0185 (14)	−0.0016 (10)	0.0086 (11)	−0.0002 (11)
N2	0.0226 (14)	0.0170 (14)	0.0156 (13)	−0.0010 (10)	0.0079 (11)	0.0006 (10)
O1	0.0115 (12)	0.0128 (12)	0.0203 (13)	−0.0008 (9)	0.0061 (10)	0.0012 (10)
O2	0.0274 (14)	0.0139 (12)	0.0178 (13)	−0.0039 (10)	0.0125 (11)	−0.0033 (11)
O3	0.0272 (15)	0.0191 (12)	0.0205 (14)	0.0079 (10)	0.0072 (12)	0.0051 (11)
O4	0.0252 (13)	0.0200 (12)	0.0170 (12)	0.0001 (10)	0.0109 (10)	0.0032 (10)
O5	0.0146 (12)	0.0199 (12)	0.0185 (12)	0.0001 (9)	0.0081 (10)	−0.0027 (10)
C1	0.0138 (14)	0.0141 (17)	0.0181 (15)	0.0027 (10)	0.0064 (12)	0.0005 (11)
C2	0.0163 (15)	0.0147 (15)	0.0158 (15)	0.0024 (11)	0.0049 (12)	0.0002 (12)
C3	0.0156 (15)	0.0140 (13)	0.0132 (14)	−0.0010 (11)	0.0065 (12)	−0.0021 (11)
C4	0.0130 (14)	0.0130 (14)	0.0135 (15)	0.0004 (11)	0.0052 (12)	−0.0024 (13)
C5	0.0108 (14)	0.0131 (13)	0.0137 (15)	−0.0002 (10)	0.0047 (12)	−0.0014 (12)
C6	0.0170 (15)	0.0132 (13)	0.0135 (15)	0.0008 (11)	0.0075 (12)	−0.0004 (12)
C7	0.038 (2)	0.0196 (17)	0.0184 (17)	−0.0027 (15)	0.0156 (16)	−0.0031 (14)
C8	0.0205 (14)	0.011 (2)	0.0169 (14)	−0.0008 (10)	0.0085 (11)	0.0021 (11)
C9	0.0175 (16)	0.0153 (15)	0.0237 (18)	−0.0017 (12)	0.0129 (14)	−0.0021 (13)
C10	0.0234 (17)	0.0175 (15)	0.0241 (18)	−0.0043 (13)	0.0149 (15)	−0.0032 (14)
C11	0.0362 (17)	0.0203 (18)	0.0148 (13)	0.001 (2)	0.0072 (12)	0.005 (2)
C12	0.042 (2)	0.030 (3)	0.0215 (16)	0.0067 (18)	0.0031 (15)	0.0061 (18)
I1	0.02599 (10)	0.01685 (9)	0.01752 (9)	0.00241 (13)	0.00673 (7)	0.00025 (13)
N3	0.0222 (16)	0.0241 (16)	0.0226 (17)	−0.0012 (13)	0.0040 (13)	0.0042 (14)
O7	0.0305 (16)	0.0392 (17)	0.0239 (15)	0.0009 (13)	0.0108 (13)	0.0044 (13)
C13	0.028 (2)	0.041 (2)	0.024 (2)	0.003 (2)	−0.0027 (18)	0.0025 (19)
C14	0.033 (2)	0.042 (2)	0.031 (2)	−0.0034 (19)	0.0139 (19)	0.005 (2)
C15	0.022 (2)	0.0260 (18)	0.022 (2)	−0.0009 (17)	0.0021 (18)	0.0034 (17)

Geometric parameters (Å, º)

N1—C8	1.324 (4)	C5—H5	1.0000
N1—C9	1.383 (4)	C6—H6A	0.9900
N1—C6	1.472 (4)	C6—H6B	0.9900
N2—C8	1.339 (4)	C7—H7A	0.9800
N2—C10	1.379 (5)	C7—H7B	0.9800
N2—C11	1.424 (4)	C7—H7C	0.9800
O1—C1	1.421 (4)	C8—H8	0.9500
O1—C5	1.446 (4)	C9—C10	1.345 (5)
O2—C1	1.396 (4)	C9—H9	0.9500
O2—C7	1.428 (5)	C10—H10	0.9500
O3—C2	1.416 (4)	C11—C12	1.298 (6)
O3—H3A	0.72 (4)	C11—H11	0.9500
O4—C3	1.430 (4)	C12—H12A	0.9500
O4—H4A	0.78 (5)	C12—H12B	0.9500
O5—C4	1.424 (4)	N3—C15	1.322 (6)
O5—H5A	0.74 (5)	N3—C14	1.442 (6)
C1—C2	1.523 (5)	N3—C13	1.453 (5)
C1—H1	1.0000	O7—C15	1.243 (5)
C2—C3	1.536 (5)	C13—H13A	0.9800
C2—H2	1.0000	C13—H13B	0.9800
C3—C4	1.523 (5)	C13—H13C	0.9800
C3—H3	1.0000	C14—H14A	0.9800
C4—C5	1.527 (5)	C14—H14B	0.9800
C4—H4	1.0000	C14—H14C	0.9800
C5—C6	1.509 (4)	C15—H15	0.9500
C8—N1—C9	108.9 (3)	C5—C6—H6A	109.6
C8—N1—C6	124.9 (3)	N1—C6—H6B	109.6
C9—N1—C6	126.0 (3)	C5—C6—H6B	109.6
C8—N2—C10	108.2 (3)	H6A—C6—H6B	108.1
C8—N2—C11	127.4 (3)	O2—C7—H7A	109.5
C10—N2—C11	124.2 (3)	O2—C7—H7B	109.5
C1—O1—C5	113.8 (3)	H7A—C7—H7B	109.5
C1—O2—C7	112.6 (3)	O2—C7—H7C	109.5
C2—O3—H3A	105 (4)	H7A—C7—H7C	109.5
C3—O4—H4A	117 (4)	H7B—C7—H7C	109.5
C4—O5—H5A	108 (3)	N1—C8—N2	108.5 (3)
O2—C1—O1	112.4 (3)	N1—C8—H8	125.8
O2—C1—C2	108.8 (3)	N2—C8—H8	125.8
O1—C1—C2	109.3 (3)	C10—C9—N1	106.9 (3)
O2—C1—H1	108.8	C10—C9—H9	126.6
O1—C1—H1	108.8	N1—C9—H9	126.6
C2—C1—H1	108.8	C9—C10—N2	107.5 (3)
O3—C2—C1	109.2 (3)	C9—C10—H10	126.2
O3—C2—C3	112.5 (3)	N2—C10—H10	126.2
C1—C2—C3	110.9 (3)	C12—C11—N2	123.8 (3)
O3—C2—H2	108.0	C12—C11—H11	118.1
C1—C2—H2	108.0	N2—C11—H11	118.1
C3—C2—H2	108.0	C11—C12—H12A	120.0
O4—C3—C4	108.1 (3)	C11—C12—H12B	120.0
O4—C3—C2	110.0 (3)	H12A—C12—H12B	120.0
C4—C3—C2	109.4 (3)	C15—N3—C14	121.8 (4)
O4—C3—H3	109.8	C15—N3—C13	121.5 (4)
C4—C3—H3	109.8	C14—N3—C13	116.7 (4)
C2—C3—H3	109.8	N3—C13—H13A	109.5
O5—C4—C3	109.9 (3)	N3—C13—H13B	109.5
O5—C4—C5	108.6 (3)	H13A—C13—H13B	109.5
C3—C4—C5	108.9 (3)	N3—C13—H13C	109.5
O5—C4—H4	109.8	H13A—C13—H13C	109.5
C3—C4—H4	109.8	H13B—C13—H13C	109.5
C5—C4—H4	109.8	N3—C14—H14A	109.5
O1—C5—C6	105.7 (3)	N3—C14—H14B	109.5
O1—C5—C4	110.4 (3)	H14A—C14—H14B	109.5
C6—C5—C4	112.8 (3)	N3—C14—H14C	109.5
O1—C5—H5	109.3	H14A—C14—H14C	109.5
C6—C5—H5	109.3	H14B—C14—H14C	109.5
C4—C5—H5	109.3	O7—C15—N3	125.3 (5)
N1—C6—C5	110.4 (3)	O7—C15—H15	117.4
N1—C6—H6A	109.6	N3—C15—H15	117.4
C7—O2—C1—O1	65.7 (4)	O5—C4—C5—C6	64.9 (3)
C7—O2—C1—C2	−173.1 (3)	C3—C4—C5—C6	−175.4 (3)
C5—O1—C1—O2	61.2 (4)	C8—N1—C6—C5	117.5 (3)
C5—O1—C1—C2	−59.7 (3)	C9—N1—C6—C5	−56.3 (4)
O2—C1—C2—O3	57.7 (3)	O1—C5—C6—N1	74.9 (3)
O1—C1—C2—O3	−179.2 (3)	C4—C5—C6—N1	−164.3 (3)
O2—C1—C2—C3	−66.8 (3)	C9—N1—C8—N2	−0.8 (4)
O1—C1—C2—C3	56.3 (3)	C6—N1—C8—N2	−175.6 (3)
O3—C2—C3—O4	63.2 (4)	C10—N2—C8—N1	0.9 (4)
C1—C2—C3—O4	−174.2 (3)	C11—N2—C8—N1	176.6 (4)
O3—C2—C3—C4	−178.2 (3)	C8—N1—C9—C10	0.5 (4)
C1—C2—C3—C4	−55.6 (3)	C6—N1—C9—C10	175.1 (3)
O4—C3—C4—O5	−66.2 (3)	N1—C9—C10—N2	0.1 (4)
C2—C3—C4—O5	174.1 (3)	C8—N2—C10—C9	−0.6 (4)
O4—C3—C4—C5	175.0 (3)	C11—N2—C10—C9	−176.5 (4)
C2—C3—C4—C5	55.3 (3)	C8—N2—C11—C12	−6.4 (8)
C1—O1—C5—C6	−176.5 (3)	C10—N2—C11—C12	168.6 (5)
C1—O1—C5—C4	61.2 (3)	C14—N3—C15—O7	−178.8 (4)
O5—C4—C5—O1	−177.0 (3)	C13—N3—C15—O7	−0.4 (7)
C3—C4—C5—O1	−57.3 (3)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
O3—H3A···O7	0.72 (4)	2.09 (4)	2.797 (4)	167 (5)
O4—H4A···I1^i	0.78 (5)	2.71 (5)	3.482 (3)	171 (4)
O5—H5A···I1	0.74 (5)	2.75 (5)	3.474 (3)	165 (4)
C6—H6A···O5^ii	0.99	2.46	3.332 (4)	147
C8—H8···O4^ii	0.95	2.44	3.252 (4)	143
C8—H8···O5^ii	0.95	2.53	3.285 (4)	136
C9—H9···O3^iii	0.95	2.51	3.404 (5)	156
C10—H10···O7^iii	0.95	2.40	3.159 (5)	137
C11—H11···I1^iv	0.95	3.02	3.925 (3)	161
C15—H15···O4	0.95	2.58	3.297 (5)	132

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