Crystal structure of 2-methyl-1H-imidazol-3-ium 3,5-di­carb­oxy­benzoate

Baletska, S.; Techert, S.; Velazquez-Garcia, J. de J.

doi:10.1107/S2056989023009209

Crystal structure of 2-methyl-1H-imidazol-3-ium 3,5-dicarboxybenzoate

S. Baletska, S. Techert and J. de J. Velazquez-Garcia

The structure of a 2-methyl-1H-imidazol-3-ium trimesate compound was determined by single-crystal X-ray diffraction. The compound is composed of protonated 2-methylimidazole and singly deprotonated trimesic acid molecules.

Keywords: crystal structure; 2-methylimidazole; trimesic acid.

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Supporting information

	Crystallographic Information File (CIF) https://doi.org/10.1107/S2056989023009209/jq2031sup1.cif Contains datablock I
	Structure factor file (CIF format) https://doi.org/10.1107/S2056989023009209/jq2031Isup2.hkl Contains datablock I
	Chemical Markup Language (CML) file https://doi.org/10.1107/S2056989023009209/jq2031Isup3.cml Supplementary material

CCDC reference: 2302266

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Key indicators

Structure: I

Single-crystal X-ray study
T = 100 K
Mean (C-C) = 0.002 Å
R factor = 0.039
wR factor = 0.103
Data-to-parameter ratio = 12.4

checkCIF/PLATON results

No syntax errors found



Alert level C
PLAT250_ALERT_2_C Large U3/U1 Ratio for Average U(i,j) Tensor ....        2.1 Note
PLAT411_ALERT_2_C Short Inter H...H Contact  H2A      ..H10      .       2.04 Ang.
                                                1-x,2-y,1-z  =      5_676 Check

Alert level G
PLAT002_ALERT_2_G Number of Distance or Angle Restraints on AtSite          7 Note
PLAT007_ALERT_5_G Number of Unrefined Donor-H Atoms ..............          5 Report
PLAT012_ALERT_1_G No       _shelx_res_checksum Found in CIF ......     Please Check
PLAT176_ALERT_4_G The CIF-Embedded .res File Contains SADI Records          3 Report
PLAT300_ALERT_4_G Atom Site Occupancy of H2         Constrained at        0.5 Check
PLAT300_ALERT_4_G Atom Site Occupancy of H3         Constrained at        0.5 Check
PLAT789_ALERT_4_G Atoms with Negative _atom_site_disorder_group  #          2 Check
PLAT802_ALERT_4_G CIF Input Record(s) with more than 80 Characters          2 Info
PLAT822_ALERT_4_G CIF-embedded .res Contains Negative PART Numbers          2 Check
PLAT860_ALERT_3_G Number of Least-Squares Restraints .............          3 Note
PLAT910_ALERT_3_G Missing # of FCF Reflection(s) Below Theta(Min).          2 Note
PLAT912_ALERT_4_G Missing # of FCF Reflections Above STh/L=  0.600          3 Note
PLAT933_ALERT_2_G Number of HKL-OMIT Records in Embedded .res File          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
   2 ALERT level C = Check. Ensure it is not caused by an omission or oversight
  14 ALERT level G = General information/check it is not something unexpected

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

Computing details top

Data collection: APEX2 (Bruker, 2016); cell refinement: SAINT (Bruker, 2016); data reduction: SAINT (Bruker, 2016); program(s) used to solve structure: SHELXT2018/2 (Sheldrick, 2015a); program(s) used to refine structure: SHELXL2018/3 (Sheldrick, 2015b); molecular graphics: Olex2 1.5 (Dolomanov et al., 2009); software used to prepare material for publication: Olex2 1.5 (Dolomanov et al., 2009).

2-Methyl-1H-imidazol-3-ium 3,5-dicarboxybenzoate top

Crystal data top

C₄H₇N₂⁺·C₉H₅O₆⁻	F(000) = 1216
M_r = 292.25	D_x = 1.582 Mg m⁻³
Monoclinic, C2/c	Mo Kα radiation, λ = 0.71073 Å
a = 24.0655 (18) Å	Cell parameters from 2955 reflections
b = 3.7704 (3) Å	θ = 2.5–30.4°
c = 27.4258 (19) Å	µ = 0.13 mm⁻¹
β = 99.481 (8)°	T = 100 K
V = 2454.5 (3) Å³	Block, clear light colourless
Z = 8	0.1 × 0.1 × 0.03 mm

Data collection top

Bruker APEX Duo CCD area detector diffractometer	1969 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.074
phi and ω scans	θ_max = 26.4°, θ_min = 2.1°
Absorption correction: multi-scan (SADABS; Krause et al., 2015)	h = −30→30
T_min = 0.628, T_max = 0.745	k = −4→4
23840 measured reflections	l = −34→34
2531 independent reflections

Refinement top

Refinement on F²	Primary atom site location: dual
Least-squares matrix: full	Hydrogen site location: mixed
R[F² > 2σ(F²)] = 0.039	H atoms treated by a mixture of independent and constrained refinement
wR(F²) = 0.103	w = 1/[σ²(F_o²) + (0.0457P)² + 3.154P] where P = (F_o² + 2F_c²)/3
S = 1.04	(Δ/σ)_max < 0.001
2531 reflections	Δρ_max = 0.24 e Å⁻³
204 parameters	Δρ_min = −0.28 e Å⁻³
3 restraints

Special details top

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 (Å²) top

	x	y	z	U_iso*/U_eq	Occ. (<1)
O5	0.21243 (5)	1.0194 (4)	0.29386 (4)	0.0167 (3)
H5	0.178804	0.950516	0.290143	0.025*
O4	0.39014 (5)	1.2973 (4)	0.22895 (4)	0.0172 (3)
O3	0.47026 (5)	1.2416 (4)	0.28243 (4)	0.0175 (3)
H3	0.484491	1.273555	0.256792	0.026*	0.5
O1	0.39873 (5)	0.7849 (4)	0.48212 (4)	0.0196 (3)
O2	0.47345 (5)	1.0439 (4)	0.45787 (4)	0.0174 (3)
H2	0.488390	1.006191	0.487304	0.026*	0.5
O6	0.21810 (5)	0.7269 (4)	0.36581 (4)	0.0186 (3)
N1	0.41365 (6)	0.4251 (4)	0.56743 (5)	0.0157 (3)
H1	0.417821	0.532713	0.539790	0.019*
N2	0.37701 (6)	0.1426 (4)	0.62208 (5)	0.0154 (3)
H2B	0.352463	0.029800	0.636906	0.018*
C2	0.41679 (7)	1.0776 (5)	0.36004 (6)	0.0127 (4)
H2A	0.456452	1.111505	0.365596	0.015*
C1	0.39023 (7)	0.9786 (5)	0.39933 (6)	0.0127 (4)
C9	0.24019 (7)	0.8931 (5)	0.33578 (6)	0.0135 (4)
C4	0.32831 (7)	1.0735 (5)	0.30481 (6)	0.0125 (4)
H4	0.306933	1.108898	0.272846	0.015*
C7	0.42279 (7)	0.9286 (5)	0.45087 (6)	0.0139 (4)
C8	0.41665 (7)	1.2307 (5)	0.27097 (6)	0.0125 (4)
C6	0.33258 (7)	0.9172 (5)	0.39079 (6)	0.0129 (4)
H6	0.314219	0.841015	0.417075	0.016*
C5	0.30162 (7)	0.9672 (5)	0.34375 (6)	0.0128 (4)
C3	0.38646 (7)	1.1280 (5)	0.31275 (6)	0.0126 (4)
C12	0.36643 (8)	0.2760 (5)	0.57639 (6)	0.0156 (4)
C10	0.45497 (8)	0.3855 (5)	0.60797 (6)	0.0162 (4)
H10	0.492702	0.467759	0.611105	0.019*
C11	0.43223 (7)	0.2087 (5)	0.64244 (7)	0.0161 (4)
H11	0.450624	0.142482	0.674491	0.019*
C13	0.31239 (8)	0.2603 (6)	0.54168 (8)	0.0238 (4)
H13A	0.308320	0.473526	0.520952	0.036*	0.47 (2)
H13B	0.281126	0.247390	0.560431	0.036*	0.47 (2)
H13C	0.311958	0.049737	0.520678	0.036*	0.47 (2)
H13D	0.2871 (17)	0.450 (11)	0.5494 (18)	0.036*	0.53 (2)
H13E	0.3175 (18)	0.267 (16)	0.5074 (8)	0.036*	0.53 (2)
H13F	0.2873 (16)	0.073 (11)	0.5495 (18)	0.036*	0.53 (2)

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
O5	0.0115 (6)	0.0275 (7)	0.0096 (6)	−0.0027 (5)	−0.0024 (5)	0.0013 (5)
O4	0.0140 (6)	0.0295 (8)	0.0073 (6)	0.0010 (5)	−0.0001 (5)	0.0032 (5)
O3	0.0119 (6)	0.0305 (8)	0.0101 (6)	−0.0004 (5)	0.0024 (5)	0.0024 (6)
O1	0.0187 (7)	0.0292 (8)	0.0105 (6)	−0.0031 (6)	0.0013 (5)	0.0052 (6)
O2	0.0132 (6)	0.0293 (8)	0.0085 (6)	−0.0020 (5)	−0.0020 (5)	0.0017 (6)
O6	0.0159 (6)	0.0265 (8)	0.0133 (6)	−0.0046 (6)	0.0019 (5)	0.0027 (6)
N1	0.0192 (8)	0.0185 (8)	0.0093 (7)	−0.0011 (6)	0.0024 (6)	0.0015 (6)
N2	0.0154 (7)	0.0171 (8)	0.0142 (7)	−0.0015 (6)	0.0043 (6)	0.0024 (6)
C2	0.0115 (8)	0.0138 (9)	0.0120 (8)	−0.0002 (7)	−0.0002 (7)	−0.0018 (7)
C1	0.0154 (8)	0.0134 (9)	0.0087 (8)	0.0003 (7)	0.0001 (7)	−0.0004 (7)
C9	0.0159 (9)	0.0153 (9)	0.0088 (8)	0.0006 (7)	0.0006 (7)	−0.0035 (7)
C4	0.0143 (8)	0.0133 (9)	0.0092 (8)	0.0008 (7)	−0.0004 (6)	0.0003 (7)
C7	0.0147 (8)	0.0170 (9)	0.0095 (8)	0.0023 (7)	0.0011 (7)	−0.0001 (7)
C8	0.0114 (8)	0.0152 (9)	0.0108 (8)	0.0000 (7)	0.0013 (6)	−0.0004 (7)
C6	0.0161 (9)	0.0139 (9)	0.0087 (8)	−0.0005 (7)	0.0018 (7)	0.0003 (7)
C5	0.0145 (8)	0.0129 (9)	0.0108 (8)	−0.0002 (7)	0.0014 (7)	−0.0015 (7)
C3	0.0155 (9)	0.0118 (9)	0.0101 (8)	0.0009 (7)	0.0013 (7)	−0.0004 (7)
C12	0.0176 (9)	0.0152 (9)	0.0136 (9)	0.0015 (7)	0.0009 (7)	−0.0013 (7)
C10	0.0152 (9)	0.0172 (9)	0.0156 (9)	−0.0003 (7)	0.0002 (7)	−0.0017 (7)
C11	0.0170 (9)	0.0181 (9)	0.0121 (9)	0.0029 (7)	−0.0002 (7)	0.0000 (7)
C13	0.0201 (10)	0.0277 (11)	0.0213 (10)	−0.0001 (8)	−0.0036 (8)	0.0003 (9)

Geometric parameters (Å, º) top

O5—H5	0.8400	C1—C6	1.388 (2)
O5—C9	1.320 (2)	C9—C5	1.485 (2)
O4—C8	1.247 (2)	C4—H4	0.9500
O3—H3	0.8400	C4—C5	1.393 (2)
O3—C8	1.277 (2)	C4—C3	1.396 (2)
O1—C7	1.235 (2)	C8—C3	1.505 (2)
O2—H2	0.8400	C6—H6	0.9500
O2—C7	1.279 (2)	C6—C5	1.392 (2)
O6—C9	1.224 (2)	C12—C13	1.481 (3)
N1—H1	0.8800	C10—H10	0.9500
N1—C12	1.326 (2)	C10—C11	1.345 (3)
N1—C10	1.372 (2)	C11—H11	0.9500
N2—H2B	0.8800	C13—H13A	0.9800
N2—C12	1.335 (2)	C13—H13B	0.9800
N2—C11	1.377 (2)	C13—H13C	0.9800
C2—H2A	0.9500	C13—H13D	0.984 (19)
C2—C1	1.391 (2)	C13—H13E	0.968 (19)
C2—C3	1.393 (2)	C13—H13F	0.976 (19)
C1—C7	1.511 (2)

C9—O5—H5	109.5	C5—C6—H6	120.0
C8—O3—H3	109.5	C4—C5—C9	121.01 (15)
C7—O2—H2	109.5	C6—C5—C9	118.60 (15)
C12—N1—H1	125.3	C6—C5—C4	120.36 (16)
C12—N1—C10	109.41 (15)	C2—C3—C4	118.91 (16)
C10—N1—H1	125.3	C2—C3—C8	119.96 (15)
C12—N2—H2B	125.2	C4—C3—C8	121.11 (15)
C12—N2—C11	109.55 (15)	N1—C12—N2	107.26 (15)
C11—N2—H2B	125.2	N1—C12—C13	125.88 (17)
C1—C2—H2A	119.3	N2—C12—C13	126.86 (17)
C1—C2—C3	121.37 (16)	N1—C10—H10	126.3
C3—C2—H2A	119.3	C11—C10—N1	107.41 (16)
C2—C1—C7	121.63 (15)	C11—C10—H10	126.3
C6—C1—C2	119.22 (16)	N2—C11—H11	126.8
C6—C1—C7	119.14 (15)	C10—C11—N2	106.37 (16)
O5—C9—C5	114.15 (15)	C10—C11—H11	126.8
O6—C9—O5	123.87 (16)	C12—C13—H13A	109.5
O6—C9—C5	121.98 (15)	C12—C13—H13B	109.5
C5—C4—H4	120.0	C12—C13—H13C	109.5
C5—C4—C3	120.01 (16)	C12—C13—H13D	110 (3)
C3—C4—H4	120.0	C12—C13—H13E	113 (3)
O1—C7—O2	126.09 (16)	C12—C13—H13F	113 (3)
O1—C7—C1	118.28 (15)	H13A—C13—H13B	109.5
O2—C7—C1	115.64 (15)	H13A—C13—H13C	109.5
O4—C8—O3	124.26 (15)	H13B—C13—H13C	109.5
O4—C8—C3	121.17 (15)	H13D—C13—H13E	112 (4)
O3—C8—C3	114.57 (15)	H13D—C13—H13F	93 (4)
C1—C6—H6	120.0	H13E—C13—H13F	114 (4)
C1—C6—C5	120.09 (16)

O5—C9—C5—C4	−16.1 (2)	C7—C1—C6—C5	178.97 (16)
O5—C9—C5—C6	165.92 (15)	C6—C1—C7—O1	10.5 (3)
O4—C8—C3—C2	−175.82 (17)	C6—C1—C7—O2	−169.07 (16)
O4—C8—C3—C4	5.7 (3)	C5—C4—C3—C2	−0.6 (3)
O3—C8—C3—C2	4.4 (2)	C5—C4—C3—C8	177.89 (16)
O3—C8—C3—C4	−174.11 (16)	C3—C2—C1—C7	−179.11 (16)
O6—C9—C5—C4	163.43 (17)	C3—C2—C1—C6	2.2 (3)
O6—C9—C5—C6	−14.5 (3)	C3—C4—C5—C9	−177.44 (16)
N1—C10—C11—N2	0.1 (2)	C3—C4—C5—C6	0.5 (3)
C2—C1—C7—O1	−168.16 (17)	C12—N1—C10—C11	−0.2 (2)
C2—C1—C7—O2	12.3 (3)	C12—N2—C11—C10	0.0 (2)
C2—C1—C6—C5	−2.3 (3)	C10—N1—C12—N2	0.1 (2)
C1—C2—C3—C4	−0.7 (3)	C10—N1—C12—C13	−179.50 (18)
C1—C2—C3—C8	−179.26 (16)	C11—N2—C12—N1	−0.1 (2)
C1—C6—C5—C9	178.97 (16)	C11—N2—C12—C13	179.56 (18)
C1—C6—C5—C4	1.0 (3)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1···O1	0.88	1.84	2.6771 (19)	159
O2—H2···O2ⁱ	0.84	1.64	2.4718 (16)	171
N2—H2B···O6ⁱⁱ	0.88	1.95	2.746 (2)	151
O3—H3···O3ⁱⁱⁱ	0.84	1.66	2.4601 (16)	159
O5—H5···O4^iv	0.84	1.75	2.5840 (18)	170

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

Selected bond lengths (Å), bond angles (°), and torsion angles (°) of the btc ion top

C1—C6	1.388 (2)	C2—C3—C4	118.91 (16)
C1—C7	1.511 (2)	C2—C1—C6	119.22 (16)
C2—C1	1.391 (3)	C5—C4—C3	120.01 (16)
C2—C3	1.393 (2)	C1—C6—C5	120.09 (16)
C4—C5	1.393 (3)	C4—C5—C6	120.36 (16)
C4—C3	1.396 (2)	C1—C2—C3	121.37 (17)
C6—C5	1.392 (2)	C2—C1—C7—O1	-168.16 (17)
C8—C3	1.505 (3)	C2—C1—C7—O2	12.3 (3)
C9—C5	1.485 (2)	C6—C1—C7—O1	10.5 (2)
O1—C7	1.236 (2)	C6—C1—C7—O2	-169.07 (16)
O2—C7	1.279 (2)	O3—C8—C3—C2	4.4 (2)
O3—C8	1.277 (2)	O3—C8—C3—C4	-174.16 (17)
O4—C8	1.247 (2)	O4—C8—C3—C2	-175.82 (17)
O5—C9	1.320 (2)	O4—C8—C3—C4	5.7 (3)
O6—C9	1.224 (2)	O5—C9—C5—C4	-16.1 (2)
O1—C7—O2	126.09 (16)	O5—C9—C5—C6	165.92 (15)
O4—C8—O3	124.26 (15)	O6—C9—C5—C4	163.43 (17)
O5—C9—O6	123.87 (16)	O6—C9—C5—C6	-14.5 (3)

Selected bond lengths (Å), bond angles (°), and torsion angles (°) of the HmIm ion top

C10—C11	1.345 (3)	N1—C12—C13	125.88 (17)
C12—C13	1.481 (3)	N2—C11—C10	106.37 (16)
N1—C12	1.327 (2)	N2—C12—C13	126.86 (17)
N1—C10	1.372 (2)	C12—N2—C11—C10	-0.0 (2)
N2—C12	1.335 (2)	C12—N1—C10—C11	-0.1 (2)
N2—C11	1.377 (2)	C10—N1—C12—C13	-179.50 (18)
C12—N1—C10	109.41 (15)	C11—N2—C12—C13	179.56 (18)
C12—N2—C11	109.55 (15)	C11—N2—C12—N1	-0.1 (2)
N1—C12—N2	107.26 (15)	C10—N1—C12—N2	0.1 (2)
N1—C10—C11	107.41 (16)	N1—C10—C11—N2	0.1 (2)

Hydrogen-bond geometry (Å, °) top

	D–H	H···A	D···A	D–H···A
N1–H1···O1	0.88	1.84	2.6771 (19)	159
O2–H2···O2ⁱ	0.84	1.64	2.4718 (16)	171
N2–H2B···O6^iv	0.88	1.95	2.7460 (20)	151
O3–H3···O3ⁱⁱ	0.84	1.66	2.4601 (16)	159
O5–H5···O4ⁱⁱⁱ	0.84	1.75	2.5840 (18)	170

(i) 1-x,2-y,1-z, (ii) 1-x,y,1/2-z, (iii) 1/2-x,-1/2+y,1/2-z, (iv) 1/2-x,1/2-y,1-z

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Crystal structure of 2-methyl-1H-imidazol-3-ium 3,5-di­carb­oxy­benzoate

Supporting information

Key indicators

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Crystal structure of 2-methyl-1H-imidazol-3-ium 3,5-dicarboxybenzoate