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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.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S2056989023009209/jq2031sup1.cif
Contains datablock I

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S2056989023009209/jq2031Isup2.hkl
Contains datablock I

cml

Chemical Markup Language (CML) file https://doi.org/10.1107/S2056989023009209/jq2031Isup3.cml
Supplementary material

CCDC reference: 2302266

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+·C9H5O6F(000) = 1216
Mr = 292.25Dx = 1.582 Mg m3
Monoclinic, C2/cMo Kα radiation, λ = 0.71073 Å
a = 24.0655 (18) ÅCell parameters from 2955 reflections
b = 3.7704 (3) Åθ = 2.5–30.4°
c = 27.4258 (19) ŵ = 0.13 mm1
β = 99.481 (8)°T = 100 K
V = 2454.5 (3) Å3Block, clear light colourless
Z = 80.1 × 0.1 × 0.03 mm
Data collection top
Bruker APEX Duo CCD area detector
diffractometer
1969 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.074
phi and ω scansθmax = 26.4°, θmin = 2.1°
Absorption correction: multi-scan
(SADABS; Krause et al., 2015)
h = 3030
Tmin = 0.628, Tmax = 0.745k = 44
23840 measured reflectionsl = 3434
2531 independent reflections
Refinement top
Refinement on F2Primary atom site location: dual
Least-squares matrix: fullHydrogen site location: mixed
R[F2 > 2σ(F2)] = 0.039H atoms treated by a mixture of independent and constrained refinement
wR(F2) = 0.103 w = 1/[σ2(Fo2) + (0.0457P)2 + 3.154P]
where P = (Fo2 + 2Fc2)/3
S = 1.04(Δ/σ)max < 0.001
2531 reflectionsΔρmax = 0.24 e Å3
204 parametersΔρmin = 0.28 e Å3
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
xyzUiso*/UeqOcc. (<1)
O50.21243 (5)1.0194 (4)0.29386 (4)0.0167 (3)
H50.1788040.9505160.2901430.025*
O40.39014 (5)1.2973 (4)0.22895 (4)0.0172 (3)
O30.47026 (5)1.2416 (4)0.28243 (4)0.0175 (3)
H30.4844911.2735550.2567920.026*0.5
O10.39873 (5)0.7849 (4)0.48212 (4)0.0196 (3)
O20.47345 (5)1.0439 (4)0.45787 (4)0.0174 (3)
H20.4883901.0061910.4873040.026*0.5
O60.21810 (5)0.7269 (4)0.36581 (4)0.0186 (3)
N10.41365 (6)0.4251 (4)0.56743 (5)0.0157 (3)
H10.4178210.5327130.5397900.019*
N20.37701 (6)0.1426 (4)0.62208 (5)0.0154 (3)
H2B0.3524630.0298000.6369060.018*
C20.41679 (7)1.0776 (5)0.36004 (6)0.0127 (4)
H2A0.4564521.1115050.3655960.015*
C10.39023 (7)0.9786 (5)0.39933 (6)0.0127 (4)
C90.24019 (7)0.8931 (5)0.33578 (6)0.0135 (4)
C40.32831 (7)1.0735 (5)0.30481 (6)0.0125 (4)
H40.3069331.1088980.2728460.015*
C70.42279 (7)0.9286 (5)0.45087 (6)0.0139 (4)
C80.41665 (7)1.2307 (5)0.27097 (6)0.0125 (4)
C60.33258 (7)0.9172 (5)0.39079 (6)0.0129 (4)
H60.3142190.8410150.4170750.016*
C50.30162 (7)0.9672 (5)0.34375 (6)0.0128 (4)
C30.38646 (7)1.1280 (5)0.31275 (6)0.0126 (4)
C120.36643 (8)0.2760 (5)0.57639 (6)0.0156 (4)
C100.45497 (8)0.3855 (5)0.60797 (6)0.0162 (4)
H100.4927020.4677590.6111050.019*
C110.43223 (7)0.2087 (5)0.64244 (7)0.0161 (4)
H110.4506240.1424820.6744910.019*
C130.31239 (8)0.2603 (6)0.54168 (8)0.0238 (4)
H13A0.3083200.4735260.5209520.036*0.47 (2)
H13B0.2811260.2473900.5604310.036*0.47 (2)
H13C0.3119580.0497370.5206780.036*0.47 (2)
H13D0.2871 (17)0.450 (11)0.5494 (18)0.036*0.53 (2)
H13E0.3175 (18)0.267 (16)0.5074 (8)0.036*0.53 (2)
H13F0.2873 (16)0.073 (11)0.5495 (18)0.036*0.53 (2)
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
O50.0115 (6)0.0275 (7)0.0096 (6)0.0027 (5)0.0024 (5)0.0013 (5)
O40.0140 (6)0.0295 (8)0.0073 (6)0.0010 (5)0.0001 (5)0.0032 (5)
O30.0119 (6)0.0305 (8)0.0101 (6)0.0004 (5)0.0024 (5)0.0024 (6)
O10.0187 (7)0.0292 (8)0.0105 (6)0.0031 (6)0.0013 (5)0.0052 (6)
O20.0132 (6)0.0293 (8)0.0085 (6)0.0020 (5)0.0020 (5)0.0017 (6)
O60.0159 (6)0.0265 (8)0.0133 (6)0.0046 (6)0.0019 (5)0.0027 (6)
N10.0192 (8)0.0185 (8)0.0093 (7)0.0011 (6)0.0024 (6)0.0015 (6)
N20.0154 (7)0.0171 (8)0.0142 (7)0.0015 (6)0.0043 (6)0.0024 (6)
C20.0115 (8)0.0138 (9)0.0120 (8)0.0002 (7)0.0002 (7)0.0018 (7)
C10.0154 (8)0.0134 (9)0.0087 (8)0.0003 (7)0.0001 (7)0.0004 (7)
C90.0159 (9)0.0153 (9)0.0088 (8)0.0006 (7)0.0006 (7)0.0035 (7)
C40.0143 (8)0.0133 (9)0.0092 (8)0.0008 (7)0.0004 (6)0.0003 (7)
C70.0147 (8)0.0170 (9)0.0095 (8)0.0023 (7)0.0011 (7)0.0001 (7)
C80.0114 (8)0.0152 (9)0.0108 (8)0.0000 (7)0.0013 (6)0.0004 (7)
C60.0161 (9)0.0139 (9)0.0087 (8)0.0005 (7)0.0018 (7)0.0003 (7)
C50.0145 (8)0.0129 (9)0.0108 (8)0.0002 (7)0.0014 (7)0.0015 (7)
C30.0155 (9)0.0118 (9)0.0101 (8)0.0009 (7)0.0013 (7)0.0004 (7)
C120.0176 (9)0.0152 (9)0.0136 (9)0.0015 (7)0.0009 (7)0.0013 (7)
C100.0152 (9)0.0172 (9)0.0156 (9)0.0003 (7)0.0002 (7)0.0017 (7)
C110.0170 (9)0.0181 (9)0.0121 (9)0.0029 (7)0.0002 (7)0.0000 (7)
C130.0201 (10)0.0277 (11)0.0213 (10)0.0001 (8)0.0036 (8)0.0003 (9)
Geometric parameters (Å, º) top
O5—H50.8400C1—C61.388 (2)
O5—C91.320 (2)C9—C51.485 (2)
O4—C81.247 (2)C4—H40.9500
O3—H30.8400C4—C51.393 (2)
O3—C81.277 (2)C4—C31.396 (2)
O1—C71.235 (2)C8—C31.505 (2)
O2—H20.8400C6—H60.9500
O2—C71.279 (2)C6—C51.392 (2)
O6—C91.224 (2)C12—C131.481 (3)
N1—H10.8800C10—H100.9500
N1—C121.326 (2)C10—C111.345 (3)
N1—C101.372 (2)C11—H110.9500
N2—H2B0.8800C13—H13A0.9800
N2—C121.335 (2)C13—H13B0.9800
N2—C111.377 (2)C13—H13C0.9800
C2—H2A0.9500C13—H13D0.984 (19)
C2—C11.391 (2)C13—H13E0.968 (19)
C2—C31.393 (2)C13—H13F0.976 (19)
C1—C71.511 (2)
C9—O5—H5109.5C5—C6—H6120.0
C8—O3—H3109.5C4—C5—C9121.01 (15)
C7—O2—H2109.5C6—C5—C9118.60 (15)
C12—N1—H1125.3C6—C5—C4120.36 (16)
C12—N1—C10109.41 (15)C2—C3—C4118.91 (16)
C10—N1—H1125.3C2—C3—C8119.96 (15)
C12—N2—H2B125.2C4—C3—C8121.11 (15)
C12—N2—C11109.55 (15)N1—C12—N2107.26 (15)
C11—N2—H2B125.2N1—C12—C13125.88 (17)
C1—C2—H2A119.3N2—C12—C13126.86 (17)
C1—C2—C3121.37 (16)N1—C10—H10126.3
C3—C2—H2A119.3C11—C10—N1107.41 (16)
C2—C1—C7121.63 (15)C11—C10—H10126.3
C6—C1—C2119.22 (16)N2—C11—H11126.8
C6—C1—C7119.14 (15)C10—C11—N2106.37 (16)
O5—C9—C5114.15 (15)C10—C11—H11126.8
O6—C9—O5123.87 (16)C12—C13—H13A109.5
O6—C9—C5121.98 (15)C12—C13—H13B109.5
C5—C4—H4120.0C12—C13—H13C109.5
C5—C4—C3120.01 (16)C12—C13—H13D110 (3)
C3—C4—H4120.0C12—C13—H13E113 (3)
O1—C7—O2126.09 (16)C12—C13—H13F113 (3)
O1—C7—C1118.28 (15)H13A—C13—H13B109.5
O2—C7—C1115.64 (15)H13A—C13—H13C109.5
O4—C8—O3124.26 (15)H13B—C13—H13C109.5
O4—C8—C3121.17 (15)H13D—C13—H13E112 (4)
O3—C8—C3114.57 (15)H13D—C13—H13F93 (4)
C1—C6—H6120.0H13E—C13—H13F114 (4)
C1—C6—C5120.09 (16)
O5—C9—C5—C416.1 (2)C7—C1—C6—C5178.97 (16)
O5—C9—C5—C6165.92 (15)C6—C1—C7—O110.5 (3)
O4—C8—C3—C2175.82 (17)C6—C1—C7—O2169.07 (16)
O4—C8—C3—C45.7 (3)C5—C4—C3—C20.6 (3)
O3—C8—C3—C24.4 (2)C5—C4—C3—C8177.89 (16)
O3—C8—C3—C4174.11 (16)C3—C2—C1—C7179.11 (16)
O6—C9—C5—C4163.43 (17)C3—C2—C1—C62.2 (3)
O6—C9—C5—C614.5 (3)C3—C4—C5—C9177.44 (16)
N1—C10—C11—N20.1 (2)C3—C4—C5—C60.5 (3)
C2—C1—C7—O1168.16 (17)C12—N1—C10—C110.2 (2)
C2—C1—C7—O212.3 (3)C12—N2—C11—C100.0 (2)
C2—C1—C6—C52.3 (3)C10—N1—C12—N20.1 (2)
C1—C2—C3—C40.7 (3)C10—N1—C12—C13179.50 (18)
C1—C2—C3—C8179.26 (16)C11—N2—C12—N10.1 (2)
C1—C6—C5—C9178.97 (16)C11—N2—C12—C13179.56 (18)
C1—C6—C5—C41.0 (3)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
N1—H1···O10.881.842.6771 (19)159
O2—H2···O2i0.841.642.4718 (16)171
N2—H2B···O6ii0.881.952.746 (2)151
O3—H3···O3iii0.841.662.4601 (16)159
O5—H5···O4iv0.841.752.5840 (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, y1/2, z+1/2.
Selected bond lengths (Å), bond angles (°), and torsion angles (°) of the btc ion top
C1—C61.388 (2)C2—C3—C4118.91 (16)
C1—C71.511 (2)C2—C1—C6119.22 (16)
C2—C11.391 (3)C5—C4—C3120.01 (16)
C2—C31.393 (2)C1—C6—C5120.09 (16)
C4—C51.393 (3)C4—C5—C6120.36 (16)
C4—C31.396 (2)C1—C2—C3121.37 (17)
C6—C51.392 (2)C2—C1—C7—O1-168.16 (17)
C8—C31.505 (3)C2—C1—C7—O212.3 (3)
C9—C51.485 (2)C6—C1—C7—O110.5 (2)
O1—C71.236 (2)C6—C1—C7—O2-169.07 (16)
O2—C71.279 (2)O3—C8—C3—C24.4 (2)
O3—C81.277 (2)O3—C8—C3—C4-174.16 (17)
O4—C81.247 (2)O4—C8—C3—C2-175.82 (17)
O5—C91.320 (2)O4—C8—C3—C45.7 (3)
O6—C91.224 (2)O5—C9—C5—C4-16.1 (2)
O1—C7—O2126.09 (16)O5—C9—C5—C6165.92 (15)
O4—C8—O3124.26 (15)O6—C9—C5—C4163.43 (17)
O5—C9—O6123.87 (16)O6—C9—C5—C6-14.5 (3)
Selected bond lengths (Å), bond angles (°), and torsion angles (°) of the HmIm ion top
C10—C111.345 (3)N1—C12—C13125.88 (17)
C12—C131.481 (3)N2—C11—C10106.37 (16)
N1—C121.327 (2)N2—C12—C13126.86 (17)
N1—C101.372 (2)C12—N2—C11—C10-0.0 (2)
N2—C121.335 (2)C12—N1—C10—C11-0.1 (2)
N2—C111.377 (2)C10—N1—C12—C13-179.50 (18)
C12—N1—C10109.41 (15)C11—N2—C12—C13179.56 (18)
C12—N2—C11109.55 (15)C11—N2—C12—N1-0.1 (2)
N1—C12—N2107.26 (15)C10—N1—C12—N20.1 (2)
N1—C10—C11107.41 (16)N1—C10—C11—N20.1 (2)
Hydrogen-bond geometry (Å, °) top
D–HH···AD···AD–H···A
N1–H1···O10.881.842.6771 (19)159
O2–H2···O2i0.841.642.4718 (16)171
N2–H2B···O6iv0.881.952.7460 (20)151
O3–H3···O3ii0.841.662.4601 (16)159
O5–H5···O4iii0.841.752.5840 (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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