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organic compounds
1H,3H-Imidazolium (R,S)-camphor-10-sulfonate
aDepartment of Chemistry, Faculty of Science, Universiti Putra Malaysia, 43400 UPM Serdang, Selangor, Malaysia, bQueen's University Ionic Liquid Laboratory (QUILL), David Keir Building, Stransmillis Road, BT9 5AG Belfast, Northern Ireland, United Kingdom, and cX-ray Crystallography Unit, School of Physics, Universiti Sains Malaysia, 11800 USM, Penang, Malaysia
*Correspondence e-mail: hkfun@usm.my
The title compound, C3H5N2+·C10H15O4S−, comprises two crystallographically independent ion pairs (A and B) in the with slightly different conformations due to the disordered methyl groups in the anion of molecule A. Two intramolecular C—H⋯O hydrogen bonds generate S(6) ring motifs. In molecule A, the methyl groups are disordered over two sets of positions with a site-ocuppancy ratio of 0.547 (9):0.453 (9). Extensive intermolecular N—H⋯O and C—H⋯O hydrogen-bonding interactions occur in the which link the molecules into a two-dimensional network parallel to the (100) plane.
Related literature
For hydrogen-bond motifs, see: Bernstein et al. (1995). For bond-length data, see: Allen et al. (1987
). For general background, see: Fukumoto et al. (2005
); Jeremić et al. (2008
).
Experimental
Crystal data
|
|
Data collection: APEX2 (Bruker, 2005); cell SAINT (Bruker, 2005
); data reduction: SAINT; program(s) used to solve structure: SHELXTL (Sheldrick, 2008
); program(s) used to refine structure: SHELXTL; molecular graphics: SHELXTL; software used to prepare material for publication: SHELXTL and PLATON (Spek, 2003
).
Supporting information
10.1107/S1600536808043742/ww2136sup1.cif
contains datablocks global, I. DOI:Structure factors: contains datablock I. DOI: 10.1107/S1600536808043742/ww2136Isup2.hkl
(R)-(-)-Camphor-10-sulfonic acid (0.05 mol, 7.504 g) was added to imidazole (0.05 mol, 3.404 g) which was first dissolved in 20 ml of methanol. The mixture was stirred (150 rpm) for 2 h at room temperature and the excess methanol was removed in vacuo at 343 K. The final product was obtained as a white solid with 97% yield. It was then dried under high vacuum for 2 days. m.p. 559.77 K. Single Crystals suitable for X-ray analysis was obtained from methanol. Anal. Calc.: C, 51.98; H, 6.71; N, 9.33; O, 21.31; S, 10.67. Found: C, 51.97; H, 6.77; N, 9.11; O, 21.38; S, 10.77%.
All the hydrogen atoms were positioned geometrically and constrained to ride with the parent atoms with Uiso(H) = 1.2 or 1.5 Ueq (O or N). In molecule A, the methyl groups are disordered over two positions and refined isotropically with a site-occupancy ratio of 0.547 (9)/0.453 (9), because anisotropic
casues non-positive definiteness for these atoms. Sufficient due to the presence of S atoms gave the correct value of the which lead to the correct given in Fig. 1. Floating origin restraint was applied automatically by SHELXL program for this P21.Data collection: APEX2 (Bruker, 2005); cell
SAINT (Bruker, 2005); data reduction: SAINT (Bruker, 2005); program(s) used to solve structure: SHELXTL (Sheldrick, 2008); program(s) used to refine structure: SHELXTL (Sheldrick, 2008); molecular graphics: SHELXTL (Sheldrick, 2008); software used to prepare material for publication: SHELXTL (Sheldrick, 2008) and PLATON (Spek, 2003).C3H5N2+·C10H15O4S− | F(000) = 640 |
Mr = 300.37 | Dx = 1.372 Mg m−3 |
Monoclinic, P21 | Mo Kα radiation, λ = 0.71073 Å |
Hall symbol: P 2yb | Cell parameters from 9809 reflections |
a = 9.1362 (2) Å | θ = 2.3–38.9° |
b = 12.0126 (2) Å | µ = 0.24 mm−1 |
c = 13.2526 (3) Å | T = 100 K |
β = 90.757 (1)° | Block, colourless |
V = 1454.34 (5) Å3 | 0.46 × 0.45 × 0.19 mm |
Z = 4 |
Bruker SMART APEXII CCD area-detector diffractometer | 9954 independent reflections |
Radiation source: fine-focus sealed tube | 9652 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.022 |
ϕ and ω scans | θmax = 32.5°, θmin = 1.5° |
Absorption correction: multi-scan (SADABS; Bruker, 2005) | h = −13→13 |
Tmin = 0.900, Tmax = 0.956 | k = −17→18 |
25973 measured reflections | l = −17→20 |
Refinement on F2 | Secondary atom site location: difference Fourier map |
Least-squares matrix: full | Hydrogen site location: inferred from neighbouring sites |
R[F2 > 2σ(F2)] = 0.031 | H-atom parameters constrained |
wR(F2) = 0.083 | w = 1/[σ2(Fo2) + (0.047P)2 + 0.3247P] where P = (Fo2 + 2Fc2)/3 |
S = 1.07 | (Δ/σ)max = 0.002 |
9954 reflections | Δρmax = 0.53 e Å−3 |
355 parameters | Δρmin = −0.34 e Å−3 |
1 restraint | Absolute structure: Flack (1983), 4199 Friedel pairs |
Primary atom site location: structure-invariant direct methods | Absolute structure parameter: 0.01 (3) |
C3H5N2+·C10H15O4S− | V = 1454.34 (5) Å3 |
Mr = 300.37 | Z = 4 |
Monoclinic, P21 | Mo Kα radiation |
a = 9.1362 (2) Å | µ = 0.24 mm−1 |
b = 12.0126 (2) Å | T = 100 K |
c = 13.2526 (3) Å | 0.46 × 0.45 × 0.19 mm |
β = 90.757 (1)° |
Bruker SMART APEXII CCD area-detector diffractometer | 9954 independent reflections |
Absorption correction: multi-scan (SADABS; Bruker, 2005) | 9652 reflections with I > 2σ(I) |
Tmin = 0.900, Tmax = 0.956 | Rint = 0.022 |
25973 measured reflections |
R[F2 > 2σ(F2)] = 0.031 | H-atom parameters constrained |
wR(F2) = 0.083 | Δρmax = 0.53 e Å−3 |
S = 1.07 | Δρmin = −0.34 e Å−3 |
9954 reflections | Absolute structure: Flack (1983), 4199 Friedel pairs |
355 parameters | Absolute structure parameter: 0.01 (3) |
1 restraint |
Experimental. The low-temperature data was collected with the Oxford Cyrosystem Cobra low-temperature attachment. |
Geometry. All e.s.d.'s (except the e.s.d. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell e.s.d.'s are taken into account individually in the estimation of e.s.d.'s in distances, angles and torsion angles; correlations between e.s.d.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell e.s.d.'s is used for estimating e.s.d.'s involving l.s. planes. |
Refinement. 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 > σ(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. |
x | y | z | Uiso*/Ueq | Occ. (<1) | |
S1A | 1.27663 (3) | 0.30766 (2) | −0.033021 (19) | 0.01112 (5) | |
O1A | 1.29170 (10) | 0.19188 (8) | 0.00012 (7) | 0.01629 (16) | |
O2A | 1.37452 (10) | 0.38323 (9) | 0.02074 (7) | 0.01975 (18) | |
O3A | 1.28934 (9) | 0.31774 (8) | −0.14282 (6) | 0.01632 (16) | |
O4A | 1.17524 (10) | 0.29350 (10) | 0.20717 (7) | 0.0227 (2) | |
C1A | 1.09258 (13) | 0.35344 (13) | −0.00674 (10) | 0.0230 (3) | |
H1AA | 1.0990 | 0.4290 | 0.0189 | 0.028* | |
H1AB | 1.0396 | 0.3569 | −0.0706 | 0.028* | |
C2A | 1.00007 (12) | 0.28760 (11) | 0.06562 (9) | 0.0161 (2) | |
C3A | 1.05299 (13) | 0.27735 (10) | 0.17433 (9) | 0.0146 (2) | |
C4A | 0.91989 (14) | 0.24497 (12) | 0.23603 (10) | 0.0206 (2) | |
H4AA | 0.8990 | 0.3005 | 0.2870 | 0.025* | |
H4AB | 0.9338 | 0.1733 | 0.2684 | 0.025* | |
C5A | 0.79837 (14) | 0.24006 (14) | 0.15568 (11) | 0.0238 (3) | |
H5AA | 0.6991 | 0.2465 | 0.1822 | 0.029* | |
C6A | 0.8249 (2) | 0.13498 (19) | 0.09277 (16) | 0.0449 (5) | |
H6AA | 0.7441 | 0.1211 | 0.0463 | 0.054* | |
H6AB | 0.8390 | 0.0703 | 0.1356 | 0.054* | |
C7A | 0.96719 (18) | 0.16430 (16) | 0.03538 (13) | 0.0334 (4) | |
H7AA | 0.9522 | 0.1576 | −0.0370 | 0.040* | |
H7AB | 1.0470 | 0.1158 | 0.0560 | 0.040* | |
C8A | 0.84295 (13) | 0.33538 (17) | 0.08391 (10) | 0.0290 (3) | |
C9A | 0.7508 (3) | 0.3652 (4) | −0.0072 (2) | 0.0259 (7)* | 0.547 (9) |
H9AA | 0.7369 | 0.3004 | −0.0486 | 0.039* | 0.547 (9) |
H9AB | 0.7993 | 0.4219 | −0.0452 | 0.039* | 0.547 (9) |
H9AC | 0.6574 | 0.3923 | 0.0143 | 0.039* | 0.547 (9) |
C9C | 0.7443 (3) | 0.3212 (4) | −0.0153 (2) | 0.0206 (8)* | 0.453 (9) |
H9CA | 0.7518 | 0.2461 | −0.0395 | 0.031* | 0.453 (9) |
H9CB | 0.7775 | 0.3717 | −0.0663 | 0.031* | 0.453 (9) |
H9CC | 0.6441 | 0.3374 | 0.0001 | 0.031* | 0.453 (9) |
C10A | 0.8557 (3) | 0.4563 (2) | 0.1473 (2) | 0.0172 (6)* | 0.547 (9) |
H10A | 0.9196 | 0.4470 | 0.2047 | 0.026* | 0.547 (9) |
H10B | 0.7604 | 0.4783 | 0.1694 | 0.026* | 0.547 (9) |
H10C | 0.8945 | 0.5127 | 0.1038 | 0.026* | 0.547 (9) |
C10C | 0.8303 (4) | 0.4391 (3) | 0.1224 (3) | 0.0212 (8)* | 0.453 (9) |
H10D | 0.7510 | 0.4773 | 0.0890 | 0.032* | 0.453 (9) |
H10E | 0.9197 | 0.4793 | 0.1123 | 0.032* | 0.453 (9) |
H10F | 0.8110 | 0.4344 | 0.1934 | 0.032* | 0.453 (9) |
N1A | 0.44499 (11) | 0.14307 (9) | 0.76374 (8) | 0.01573 (18)* | |
H1AC | 0.3885 | 0.1977 | 0.7787 | 0.019* | |
N2A | 0.56872 (12) | 0.02395 (9) | 0.67786 (8) | 0.01563 (18) | |
H2AA | 0.6054 | −0.0114 | 0.6278 | 0.019* | |
C11A | 0.47931 (13) | 0.11135 (11) | 0.67088 (9) | 0.0155 (2) | |
H11A | 0.4466 | 0.1445 | 0.6113 | 0.019* | |
C12A | 0.51470 (14) | 0.07405 (12) | 0.83219 (9) | 0.0176 (2) | |
H12A | 0.5091 | 0.0780 | 0.9021 | 0.021* | |
C13A | 0.59299 (14) | −0.00070 (11) | 0.77835 (10) | 0.0177 (2) | |
H13A | 0.6516 | −0.0575 | 0.8042 | 0.021* | |
S1B | 1.29554 (3) | 0.33636 (2) | 0.532398 (19) | 0.01117 (5) | |
O1B | 1.30840 (10) | 0.45125 (8) | 0.49628 (7) | 0.01658 (16) | |
O2B | 1.32660 (9) | 0.32743 (8) | 0.64062 (6) | 0.01474 (15) | |
O3B | 1.37993 (10) | 0.25718 (8) | 0.47370 (7) | 0.01687 (17) | |
O4B | 0.95635 (13) | 0.47418 (10) | 0.40752 (8) | 0.0267 (2) | |
C1B | 1.10979 (12) | 0.29462 (11) | 0.51462 (9) | 0.0165 (2) | |
H1BA | 1.0902 | 0.2916 | 0.4426 | 0.020* | |
H1BB | 1.1005 | 0.2193 | 0.5402 | 0.020* | |
C2B | 0.98994 (12) | 0.36491 (10) | 0.56233 (9) | 0.0141 (2) | |
C3B | 0.91119 (14) | 0.44242 (11) | 0.48786 (10) | 0.0186 (2) | |
C4B | 0.76277 (16) | 0.46991 (13) | 0.53347 (11) | 0.0233 (3) | |
H4BA | 0.6828 | 0.4448 | 0.4903 | 0.028* | |
H4BB | 0.7526 | 0.5491 | 0.5456 | 0.028* | |
C5B | 0.76907 (13) | 0.40436 (11) | 0.63263 (10) | 0.0185 (2) | |
H5BA | 0.6734 | 0.3897 | 0.6625 | 0.022* | |
C6B | 0.87688 (15) | 0.46647 (12) | 0.70195 (11) | 0.0217 (2) | |
H6BA | 0.8732 | 0.4381 | 0.7704 | 0.026* | |
H6BB | 0.8563 | 0.5457 | 0.7026 | 0.026* | |
C7B | 1.02824 (14) | 0.44215 (12) | 0.65360 (11) | 0.0199 (2) | |
H7BA | 1.0933 | 0.4049 | 0.7012 | 0.024* | |
H7BB | 1.0743 | 0.5104 | 0.6311 | 0.024* | |
C8B | 0.85559 (12) | 0.29851 (11) | 0.60317 (9) | 0.0154 (2) | |
C9B | 0.89102 (17) | 0.22292 (13) | 0.69361 (11) | 0.0244 (3) | |
H9BA | 0.8036 | 0.1854 | 0.7143 | 0.037* | |
H9BB | 0.9285 | 0.2672 | 0.7485 | 0.037* | |
H9BC | 0.9631 | 0.1690 | 0.6746 | 0.037* | |
C10B | 0.78064 (14) | 0.22785 (12) | 0.52073 (11) | 0.0207 (2) | |
H10G | 0.6992 | 0.1888 | 0.5490 | 0.031* | |
H10H | 0.8494 | 0.1752 | 0.4945 | 0.031* | |
H10I | 0.7465 | 0.2755 | 0.4672 | 0.031* | |
N1B | 0.42936 (11) | 0.12226 (9) | 0.17235 (8) | 0.01373 (17) | |
H1BC | 0.3802 | 0.1537 | 0.1244 | 0.016* | |
N2B | 0.56682 (11) | 0.00652 (9) | 0.25337 (9) | 0.01636 (19) | |
H2BA | 0.6221 | −0.0496 | 0.2668 | 0.020* | |
C11B | 0.50552 (13) | 0.02832 (11) | 0.16403 (9) | 0.0153 (2) | |
H11B | 0.5143 | −0.0145 | 0.1060 | 0.018* | |
C12B | 0.44173 (13) | 0.16124 (11) | 0.27007 (9) | 0.0154 (2) | |
H12B | 0.3992 | 0.2253 | 0.2960 | 0.018* | |
C13B | 0.52797 (14) | 0.08788 (11) | 0.32086 (9) | 0.0171 (2) | |
H13B | 0.5556 | 0.0918 | 0.3886 | 0.021* |
U11 | U22 | U33 | U12 | U13 | U23 | |
S1A | 0.01090 (10) | 0.01332 (11) | 0.00917 (10) | 0.00054 (8) | 0.00172 (8) | 0.00011 (8) |
O1A | 0.0197 (4) | 0.0149 (4) | 0.0142 (4) | 0.0028 (3) | −0.0013 (3) | 0.0028 (3) |
O2A | 0.0213 (4) | 0.0211 (5) | 0.0168 (4) | −0.0046 (3) | −0.0011 (3) | −0.0040 (3) |
O3A | 0.0219 (4) | 0.0171 (4) | 0.0101 (3) | 0.0017 (3) | 0.0030 (3) | 0.0002 (3) |
O4A | 0.0188 (4) | 0.0302 (6) | 0.0189 (4) | 0.0012 (4) | −0.0020 (3) | −0.0005 (4) |
C1A | 0.0152 (5) | 0.0307 (7) | 0.0232 (6) | 0.0082 (5) | 0.0075 (4) | 0.0153 (5) |
C2A | 0.0115 (4) | 0.0247 (6) | 0.0120 (5) | 0.0004 (4) | 0.0019 (3) | 0.0015 (4) |
C3A | 0.0164 (5) | 0.0129 (5) | 0.0146 (5) | 0.0023 (4) | 0.0019 (4) | 0.0019 (4) |
C4A | 0.0213 (5) | 0.0236 (6) | 0.0171 (5) | 0.0022 (5) | 0.0067 (4) | 0.0062 (5) |
C5A | 0.0161 (5) | 0.0345 (8) | 0.0211 (6) | −0.0054 (5) | 0.0068 (4) | −0.0012 (5) |
C6A | 0.0342 (8) | 0.0530 (12) | 0.0480 (10) | −0.0286 (8) | 0.0241 (8) | −0.0278 (9) |
C7A | 0.0280 (7) | 0.0392 (9) | 0.0333 (8) | −0.0180 (6) | 0.0153 (6) | −0.0200 (7) |
C8A | 0.0121 (5) | 0.0538 (10) | 0.0212 (6) | 0.0088 (6) | 0.0043 (4) | 0.0164 (6) |
N2A | 0.0192 (4) | 0.0139 (5) | 0.0138 (4) | 0.0027 (3) | 0.0020 (3) | 0.0009 (3) |
C11A | 0.0179 (5) | 0.0141 (5) | 0.0146 (5) | 0.0019 (4) | 0.0010 (4) | 0.0013 (4) |
C12A | 0.0200 (5) | 0.0203 (6) | 0.0124 (5) | 0.0010 (4) | 0.0012 (4) | 0.0017 (4) |
C13A | 0.0195 (5) | 0.0186 (6) | 0.0151 (5) | 0.0032 (4) | 0.0009 (4) | 0.0034 (4) |
S1B | 0.01270 (10) | 0.01178 (11) | 0.00904 (10) | 0.00008 (8) | 0.00085 (8) | −0.00100 (8) |
O1B | 0.0207 (4) | 0.0140 (4) | 0.0151 (4) | −0.0021 (3) | 0.0020 (3) | 0.0028 (3) |
O2B | 0.0204 (4) | 0.0147 (4) | 0.0091 (3) | 0.0010 (3) | −0.0011 (3) | −0.0004 (3) |
O3B | 0.0161 (4) | 0.0197 (4) | 0.0148 (4) | 0.0036 (3) | 0.0019 (3) | −0.0045 (3) |
O4B | 0.0345 (5) | 0.0241 (5) | 0.0217 (5) | −0.0021 (4) | 0.0052 (4) | 0.0054 (4) |
C1B | 0.0143 (4) | 0.0160 (5) | 0.0192 (5) | −0.0007 (4) | 0.0007 (4) | −0.0069 (4) |
C2B | 0.0132 (4) | 0.0127 (5) | 0.0164 (5) | −0.0005 (3) | 0.0020 (4) | −0.0034 (4) |
C3B | 0.0216 (5) | 0.0129 (5) | 0.0213 (6) | −0.0010 (4) | 0.0023 (4) | −0.0001 (4) |
C4B | 0.0219 (6) | 0.0204 (6) | 0.0277 (7) | 0.0068 (5) | 0.0021 (5) | 0.0034 (5) |
C5B | 0.0154 (5) | 0.0174 (6) | 0.0230 (6) | 0.0023 (4) | 0.0050 (4) | −0.0003 (4) |
C6B | 0.0206 (5) | 0.0207 (6) | 0.0239 (6) | 0.0017 (4) | 0.0057 (5) | −0.0081 (5) |
C7B | 0.0170 (5) | 0.0200 (6) | 0.0227 (6) | −0.0009 (4) | 0.0038 (4) | −0.0099 (5) |
C8B | 0.0155 (4) | 0.0143 (5) | 0.0165 (5) | −0.0011 (4) | 0.0031 (4) | 0.0005 (4) |
C9B | 0.0316 (7) | 0.0209 (7) | 0.0208 (6) | 0.0027 (5) | 0.0048 (5) | 0.0050 (5) |
C10B | 0.0185 (5) | 0.0195 (6) | 0.0243 (6) | −0.0061 (4) | 0.0019 (4) | −0.0039 (5) |
N1B | 0.0142 (4) | 0.0156 (5) | 0.0114 (4) | 0.0014 (3) | −0.0004 (3) | 0.0017 (3) |
N2B | 0.0139 (4) | 0.0138 (5) | 0.0214 (5) | 0.0016 (3) | 0.0000 (4) | 0.0036 (4) |
C11B | 0.0145 (5) | 0.0149 (5) | 0.0165 (5) | 0.0000 (4) | 0.0026 (4) | −0.0016 (4) |
C12B | 0.0167 (5) | 0.0162 (5) | 0.0132 (5) | 0.0013 (4) | 0.0020 (4) | −0.0015 (4) |
C13B | 0.0184 (5) | 0.0193 (6) | 0.0136 (5) | −0.0026 (4) | −0.0007 (4) | 0.0029 (4) |
S1A—O2A | 1.4542 (10) | C11A—H11A | 0.9300 |
S1A—O1A | 1.4645 (9) | C12A—C13A | 1.3566 (18) |
S1A—O3A | 1.4663 (8) | C12A—H12A | 0.9300 |
S1A—C1A | 1.8074 (12) | C13A—H13A | 0.9300 |
O4A—C3A | 1.2090 (15) | S1B—O3B | 1.4560 (9) |
C1A—C2A | 1.5102 (17) | S1B—O2B | 1.4622 (8) |
C1A—H1AA | 0.9700 | S1B—O1B | 1.4661 (9) |
C1A—H1AB | 0.9700 | S1B—C1B | 1.7822 (12) |
C2A—C3A | 1.5185 (16) | O4B—C3B | 1.2088 (17) |
C2A—C7A | 1.563 (2) | C1B—C2B | 1.5264 (16) |
C2A—C8A | 1.5678 (17) | C1B—H1BA | 0.9700 |
C3A—C4A | 1.5248 (17) | C1B—H1BB | 0.9700 |
C4A—C5A | 1.529 (2) | C2B—C3B | 1.5297 (18) |
C4A—H4AA | 0.9700 | C2B—C7B | 1.5606 (18) |
C4A—H4AB | 0.9700 | C2B—C8B | 1.5663 (16) |
C5A—C6A | 1.534 (2) | C3B—C4B | 1.5280 (19) |
C5A—C8A | 1.547 (2) | C4B—C5B | 1.532 (2) |
C5A—H5AA | 0.9800 | C4B—H4BA | 0.9700 |
C6A—C7A | 1.555 (2) | C4B—H4BB | 0.9700 |
C6A—H6AA | 0.9700 | C5B—C6B | 1.532 (2) |
C6A—H6AB | 0.9700 | C5B—C8B | 1.5499 (18) |
C7A—H7AA | 0.9700 | C5B—H5BA | 0.9800 |
C7A—H7AB | 0.9700 | C6B—C7B | 1.5593 (18) |
C8A—C10C | 1.352 (5) | C6B—H6BA | 0.9700 |
C8A—C9A | 1.506 (3) | C6B—H6BB | 0.9700 |
C8A—C9C | 1.594 (3) | C7B—H7BA | 0.9700 |
C8A—C10A | 1.681 (4) | C7B—H7BB | 0.9700 |
C9A—H9AA | 0.9600 | C8B—C9B | 1.5347 (19) |
C9A—H9AB | 0.9600 | C8B—C10B | 1.5374 (18) |
C9A—H9AC | 0.9600 | C9B—H9BA | 0.9600 |
C9C—H9CA | 0.9600 | C9B—H9BB | 0.9600 |
C9C—H9CB | 0.9600 | C9B—H9BC | 0.9600 |
C9C—H9CC | 0.9600 | C10B—H10G | 0.9600 |
C10A—H10A | 0.9600 | C10B—H10H | 0.9600 |
C10A—H10B | 0.9600 | C10B—H10I | 0.9600 |
C10A—H10C | 0.9600 | N1B—C11B | 1.3311 (16) |
C10C—H10D | 0.9600 | N1B—C12B | 1.3803 (15) |
C10C—H10E | 0.9600 | N1B—H1BC | 0.8600 |
C10C—H10F | 0.9600 | N2B—C11B | 1.3291 (16) |
N1A—C11A | 1.3297 (16) | N2B—C13B | 1.3747 (17) |
N1A—C12A | 1.3786 (17) | N2B—H2BA | 0.8600 |
N1A—H1AC | 0.8600 | C11B—H11B | 0.9300 |
N2A—C11A | 1.3327 (16) | C12B—C13B | 1.3552 (18) |
N2A—C13A | 1.3793 (16) | C12B—H12B | 0.9300 |
N2A—H2AA | 0.8600 | C13B—H13B | 0.9300 |
O2A—S1A—O1A | 113.02 (6) | C13A—N2A—H2AA | 125.5 |
O2A—S1A—O3A | 112.24 (6) | N1A—C11A—N2A | 108.26 (11) |
O1A—S1A—O3A | 111.57 (5) | N1A—C11A—H11A | 125.9 |
O2A—S1A—C1A | 106.46 (7) | N2A—C11A—H11A | 125.9 |
O1A—S1A—C1A | 108.37 (6) | C13A—C12A—N1A | 107.11 (11) |
O3A—S1A—C1A | 104.61 (6) | C13A—C12A—H12A | 126.4 |
C2A—C1A—S1A | 119.53 (9) | N1A—C12A—H12A | 126.4 |
C2A—C1A—H1AA | 107.4 | C12A—C13A—N2A | 106.65 (11) |
S1A—C1A—H1AA | 107.4 | C12A—C13A—H13A | 126.7 |
C2A—C1A—H1AB | 107.4 | N2A—C13A—H13A | 126.7 |
S1A—C1A—H1AB | 107.4 | O3B—S1B—O2B | 112.27 (5) |
H1AA—C1A—H1AB | 107.0 | O3B—S1B—O1B | 113.28 (6) |
C1A—C2A—C3A | 118.10 (11) | O2B—S1B—O1B | 111.96 (5) |
C1A—C2A—C7A | 116.16 (11) | O3B—S1B—C1B | 104.81 (5) |
C3A—C2A—C7A | 102.95 (11) | O2B—S1B—C1B | 106.33 (5) |
C1A—C2A—C8A | 115.32 (11) | O1B—S1B—C1B | 107.57 (6) |
C3A—C2A—C8A | 99.42 (9) | C2B—C1B—S1B | 118.47 (8) |
C7A—C2A—C8A | 102.31 (12) | C2B—C1B—H1BA | 107.7 |
O4A—C3A—C2A | 127.55 (11) | S1B—C1B—H1BA | 107.7 |
O4A—C3A—C4A | 125.97 (11) | C2B—C1B—H1BB | 107.7 |
C2A—C3A—C4A | 106.46 (10) | S1B—C1B—H1BB | 107.7 |
C3A—C4A—C5A | 102.31 (10) | H1BA—C1B—H1BB | 107.1 |
C3A—C4A—H4AA | 111.3 | C1B—C2B—C3B | 113.79 (10) |
C5A—C4A—H4AA | 111.3 | C1B—C2B—C7B | 119.69 (10) |
C3A—C4A—H4AB | 111.3 | C3B—C2B—C7B | 103.70 (10) |
C5A—C4A—H4AB | 111.3 | C1B—C2B—C8B | 115.55 (10) |
H4AA—C4A—H4AB | 109.2 | C3B—C2B—C8B | 99.72 (9) |
C4A—C5A—C6A | 106.96 (14) | C7B—C2B—C8B | 101.75 (9) |
C4A—C5A—C8A | 101.83 (11) | O4B—C3B—C4B | 126.53 (13) |
C6A—C5A—C8A | 103.31 (13) | O4B—C3B—C2B | 126.68 (12) |
C4A—C5A—H5AA | 114.5 | C4B—C3B—C2B | 106.78 (10) |
C6A—C5A—H5AA | 114.5 | C3B—C4B—C5B | 101.81 (10) |
C8A—C5A—H5AA | 114.5 | C3B—C4B—H4BA | 111.4 |
C5A—C6A—C7A | 102.63 (13) | C5B—C4B—H4BA | 111.4 |
C5A—C6A—H6AA | 111.2 | C3B—C4B—H4BB | 111.4 |
C7A—C6A—H6AA | 111.2 | C5B—C4B—H4BB | 111.4 |
C5A—C6A—H6AB | 111.2 | H4BA—C4B—H4BB | 109.3 |
C7A—C6A—H6AB | 111.2 | C6B—C5B—C4B | 106.29 (12) |
H6AA—C6A—H6AB | 109.2 | C6B—C5B—C8B | 102.98 (10) |
C6A—C7A—C2A | 104.38 (13) | C4B—C5B—C8B | 102.65 (10) |
C6A—C7A—H7AA | 110.9 | C6B—C5B—H5BA | 114.5 |
C2A—C7A—H7AA | 110.9 | C4B—C5B—H5BA | 114.5 |
C6A—C7A—H7AB | 110.9 | C8B—C5B—H5BA | 114.5 |
C2A—C7A—H7AB | 110.9 | C5B—C6B—C7B | 103.23 (10) |
H7AA—C7A—H7AB | 108.9 | C5B—C6B—H6BA | 111.1 |
C10C—C8A—C9A | 91.9 (2) | C7B—C6B—H6BA | 111.1 |
C10C—C8A—C5A | 115.18 (19) | C5B—C6B—H6BB | 111.1 |
C9A—C8A—C5A | 121.34 (19) | C7B—C6B—H6BB | 111.1 |
C10C—C8A—C2A | 118.6 (2) | H6BA—C6B—H6BB | 109.1 |
C9A—C8A—C2A | 117.82 (16) | C6B—C7B—C2B | 103.83 (10) |
C5A—C8A—C2A | 94.20 (11) | C6B—C7B—H7BA | 111.0 |
C10C—C8A—C9C | 111.1 (2) | C2B—C7B—H7BA | 111.0 |
C9A—C8A—C9C | 19.89 (13) | C6B—C7B—H7BB | 111.0 |
C5A—C8A—C9C | 106.14 (19) | C2B—C7B—H7BB | 111.0 |
C2A—C8A—C9C | 110.03 (16) | H7BA—C7B—H7BB | 109.0 |
C10C—C8A—C10A | 11.72 (18) | C9B—C8B—C10B | 108.40 (11) |
C9A—C8A—C10A | 103.2 (2) | C9B—C8B—C5B | 113.06 (11) |
C5A—C8A—C10A | 110.47 (13) | C10B—C8B—C5B | 114.08 (10) |
C2A—C8A—C10A | 109.62 (14) | C9B—C8B—C2B | 114.39 (10) |
C9C—C8A—C10A | 122.6 (2) | C10B—C8B—C2B | 112.29 (10) |
C8A—C9A—H9AA | 109.5 | C5B—C8B—C2B | 94.24 (9) |
C8A—C9A—H9AB | 109.5 | C8B—C9B—H9BA | 109.5 |
H9AA—C9A—H9AB | 109.5 | C8B—C9B—H9BB | 109.5 |
C8A—C9A—H9AC | 109.5 | H9BA—C9B—H9BB | 109.5 |
H9AA—C9A—H9AC | 109.5 | C8B—C9B—H9BC | 109.5 |
H9AB—C9A—H9AC | 109.5 | H9BA—C9B—H9BC | 109.5 |
C8A—C9C—H9CA | 109.5 | H9BB—C9B—H9BC | 109.5 |
C8A—C9C—H9CB | 109.5 | C8B—C10B—H10G | 109.5 |
H9CA—C9C—H9CB | 109.5 | C8B—C10B—H10H | 109.5 |
C8A—C9C—H9CC | 109.5 | H10G—C10B—H10H | 109.5 |
H9CA—C9C—H9CC | 109.5 | C8B—C10B—H10I | 109.5 |
H9CB—C9C—H9CC | 109.5 | H10G—C10B—H10I | 109.5 |
C8A—C10A—H10A | 109.5 | H10H—C10B—H10I | 109.5 |
C8A—C10A—H10B | 109.5 | C11B—N1B—C12B | 109.21 (10) |
H10A—C10A—H10B | 109.5 | C11B—N1B—H1BC | 125.4 |
C8A—C10A—H10C | 109.5 | C12B—N1B—H1BC | 125.4 |
H10A—C10A—H10C | 109.5 | C11B—N2B—C13B | 109.28 (11) |
H10B—C10A—H10C | 109.5 | C11B—N2B—H2BA | 125.4 |
C8A—C10C—H10D | 109.5 | C13B—N2B—H2BA | 125.4 |
C8A—C10C—H10E | 109.5 | N2B—C11B—N1B | 107.93 (11) |
H10D—C10C—H10E | 109.5 | N2B—C11B—H11B | 126.0 |
C8A—C10C—H10F | 109.5 | N1B—C11B—H11B | 126.0 |
H10D—C10C—H10F | 109.5 | C13B—C12B—N1B | 106.57 (11) |
H10E—C10C—H10F | 109.5 | C13B—C12B—H12B | 126.7 |
C11A—N1A—C12A | 108.91 (11) | N1B—C12B—H12B | 126.7 |
C11A—N1A—H1AC | 125.5 | C12B—C13B—N2B | 107.01 (11) |
C12A—N1A—H1AC | 125.5 | C12B—C13B—H13B | 126.5 |
C11A—N2A—C13A | 109.07 (11) | N2B—C13B—H13B | 126.5 |
C11A—N2A—H2AA | 125.5 | ||
O2A—S1A—C1A—C2A | −105.42 (12) | C12A—N1A—C11A—N2A | 0.11 (14) |
O1A—S1A—C1A—C2A | 16.45 (14) | C13A—N2A—C11A—N1A | −0.31 (14) |
O3A—S1A—C1A—C2A | 135.58 (11) | C11A—N1A—C12A—C13A | 0.14 (15) |
S1A—C1A—C2A—C3A | 62.08 (16) | N1A—C12A—C13A—N2A | −0.32 (15) |
S1A—C1A—C2A—C7A | −60.97 (16) | C11A—N2A—C13A—C12A | 0.40 (15) |
S1A—C1A—C2A—C8A | 179.34 (11) | O3B—S1B—C1B—C2B | −176.85 (9) |
C1A—C2A—C3A—O4A | −18.12 (19) | O2B—S1B—C1B—C2B | 64.08 (11) |
C7A—C2A—C3A—O4A | 111.36 (15) | O1B—S1B—C1B—C2B | −56.02 (11) |
C8A—C2A—C3A—O4A | −143.57 (14) | S1B—C1B—C2B—C3B | 101.52 (11) |
C1A—C2A—C3A—C4A | 160.54 (11) | S1B—C1B—C2B—C7B | −21.79 (16) |
C7A—C2A—C3A—C4A | −69.99 (12) | S1B—C1B—C2B—C8B | −143.94 (9) |
C8A—C2A—C3A—C4A | 35.08 (13) | C1B—C2B—C3B—O4B | −20.75 (19) |
O4A—C3A—C4A—C5A | 178.27 (13) | C7B—C2B—C3B—O4B | 110.90 (15) |
C2A—C3A—C4A—C5A | −0.41 (13) | C8B—C2B—C3B—O4B | −144.36 (14) |
C3A—C4A—C5A—C6A | 72.78 (14) | C1B—C2B—C3B—C4B | 157.98 (11) |
C3A—C4A—C5A—C8A | −35.27 (14) | C7B—C2B—C3B—C4B | −70.38 (12) |
C4A—C5A—C6A—C7A | −68.92 (19) | C8B—C2B—C3B—C4B | 34.36 (12) |
C8A—C5A—C6A—C7A | 38.09 (18) | O4B—C3B—C4B—C5B | 178.76 (14) |
C5A—C6A—C7A—C2A | −4.3 (2) | C2B—C3B—C4B—C5B | 0.04 (14) |
C1A—C2A—C7A—C6A | −156.62 (14) | C3B—C4B—C5B—C6B | 72.54 (13) |
C3A—C2A—C7A—C6A | 72.72 (16) | C3B—C4B—C5B—C8B | −35.24 (13) |
C8A—C2A—C7A—C6A | −30.11 (17) | C4B—C5B—C6B—C7B | −71.47 (13) |
C4A—C5A—C8A—C10C | −68.8 (2) | C8B—C5B—C6B—C7B | 36.08 (13) |
C6A—C5A—C8A—C10C | −179.6 (2) | C5B—C6B—C7B—C2B | −1.55 (14) |
C4A—C5A—C8A—C9A | −178.0 (2) | C1B—C2B—C7B—C6B | −161.59 (11) |
C6A—C5A—C8A—C9A | 71.1 (2) | C3B—C2B—C7B—C6B | 70.33 (12) |
C4A—C5A—C8A—C2A | 55.64 (13) | C8B—C2B—C7B—C6B | −32.87 (13) |
C6A—C5A—C8A—C2A | −55.21 (14) | C6B—C5B—C8B—C9B | 63.83 (13) |
C4A—C5A—C8A—C9C | 167.90 (17) | C4B—C5B—C8B—C9B | 174.13 (11) |
C6A—C5A—C8A—C9C | 57.05 (19) | C6B—C5B—C8B—C10B | −171.69 (11) |
C4A—C5A—C8A—C10A | −57.12 (16) | C4B—C5B—C8B—C10B | −61.40 (13) |
C6A—C5A—C8A—C10A | −167.96 (15) | C6B—C5B—C8B—C2B | −54.96 (11) |
C1A—C2A—C8A—C10C | −60.1 (2) | C4B—C5B—C8B—C2B | 55.33 (11) |
C3A—C2A—C8A—C10C | 67.3 (2) | C1B—C2B—C8B—C9B | 66.55 (14) |
C7A—C2A—C8A—C10C | 172.9 (2) | C3B—C2B—C8B—C9B | −171.07 (11) |
C1A—C2A—C8A—C9A | 49.3 (3) | C7B—C2B—C8B—C9B | −64.75 (13) |
C3A—C2A—C8A—C9A | 176.6 (2) | C1B—C2B—C8B—C10B | −57.54 (14) |
C7A—C2A—C8A—C9A | −77.8 (3) | C3B—C2B—C8B—C10B | 64.84 (12) |
C1A—C2A—C8A—C5A | 178.22 (12) | C7B—C2B—C8B—C10B | 171.16 (11) |
C3A—C2A—C8A—C5A | −54.43 (12) | C1B—C2B—C8B—C5B | −175.74 (10) |
C7A—C2A—C8A—C5A | 51.17 (13) | C3B—C2B—C8B—C5B | −53.37 (10) |
C1A—C2A—C8A—C9C | 69.4 (2) | C7B—C2B—C8B—C5B | 52.95 (11) |
C3A—C2A—C8A—C9C | −163.3 (2) | C13B—N2B—C11B—N1B | 0.55 (14) |
C7A—C2A—C8A—C9C | −57.7 (2) | C12B—N1B—C11B—N2B | −0.35 (14) |
C1A—C2A—C8A—C10A | −68.30 (16) | C11B—N1B—C12B—C13B | 0.01 (14) |
C3A—C2A—C8A—C10A | 59.06 (15) | N1B—C12B—C13B—N2B | 0.32 (13) |
C7A—C2A—C8A—C10A | 164.65 (14) | C11B—N2B—C13B—C12B | −0.54 (14) |
D—H···A | D—H | H···A | D···A | D—H···A |
N1A—H1AC···O2Bi | 0.86 | 2.46 | 2.9479 (14) | 116 |
N1A—H1AC···O3Aii | 0.86 | 2.00 | 2.8293 (14) | 161 |
N2A—H2AA···O1Biii | 0.86 | 1.89 | 2.7235 (14) | 164 |
N1B—H1BC···O1Ai | 0.86 | 1.88 | 2.7231 (14) | 165 |
N2B—H2BA···O2Biii | 0.86 | 1.97 | 2.7412 (14) | 148 |
N2B—H2BA···O3Aiv | 0.86 | 2.43 | 3.0111 (14) | 125 |
C7A—H7AB···O1A | 0.97 | 2.53 | 3.0257 (19) | 111 |
C11A—H11A···O2Bi | 0.93 | 2.49 | 2.9716 (16) | 113 |
C11A—H11A···O3Bi | 0.93 | 2.35 | 3.2648 (15) | 170 |
C11B—H11B···O2Aiv | 0.93 | 2.33 | 3.2103 (16) | 159 |
C9A—H9AC···O2Ai | 0.96 | 2.59 | 3.469 (3) | 152 |
C12B—H12B···O3Bi | 0.93 | 2.39 | 2.9950 (15) | 122 |
C12B—H12B···O4Ai | 0.93 | 2.49 | 3.0155 (16) | 116 |
C13A—H13A···O2Aiii | 0.93 | 2.44 | 3.0167 (16) | 120 |
C13A—H13A···O4Aiii | 0.93 | 2.39 | 3.2591 (17) | 155 |
C13B—H13B···O1Biii | 0.93 | 2.58 | 3.2720 (16) | 131 |
C7B—H7BA···O2B | 0.97 | 2.47 | 3.0613 (16) | 119 |
C5A—H5AA···Cg1 | 0.98 | 2.83 | 3.5459 (5) | 131 |
Symmetry codes: (i) x−1, y, z; (ii) x−1, y, z+1; (iii) −x+2, y−1/2, −z+1; (iv) −x+2, y−1/2, −z. |
Experimental details
Crystal data | |
Chemical formula | C3H5N2+·C10H15O4S− |
Mr | 300.37 |
Crystal system, space group | Monoclinic, P21 |
Temperature (K) | 100 |
a, b, c (Å) | 9.1362 (2), 12.0126 (2), 13.2526 (3) |
β (°) | 90.757 (1) |
V (Å3) | 1454.34 (5) |
Z | 4 |
Radiation type | Mo Kα |
µ (mm−1) | 0.24 |
Crystal size (mm) | 0.46 × 0.45 × 0.19 |
Data collection | |
Diffractometer | Bruker SMART APEXII CCD area-detector diffractometer |
Absorption correction | Multi-scan (SADABS; Bruker, 2005) |
Tmin, Tmax | 0.900, 0.956 |
No. of measured, independent and observed [I > 2σ(I)] reflections | 25973, 9954, 9652 |
Rint | 0.022 |
(sin θ/λ)max (Å−1) | 0.756 |
Refinement | |
R[F2 > 2σ(F2)], wR(F2), S | 0.031, 0.083, 1.07 |
No. of reflections | 9954 |
No. of parameters | 355 |
No. of restraints | 1 |
H-atom treatment | H-atom parameters constrained |
Δρmax, Δρmin (e Å−3) | 0.53, −0.34 |
Absolute structure | Flack (1983), 4199 Friedel pairs |
Absolute structure parameter | 0.01 (3) |
Computer programs: APEX2 (Bruker, 2005), SAINT (Bruker, 2005), SHELXTL (Sheldrick, 2008) and PLATON (Spek, 2003).
D—H···A | D—H | H···A | D···A | D—H···A |
N1A—H1AC···O2Bi | 0.8600 | 2.4600 | 2.9479 (14) | 116.00 |
N1A—H1AC···O3Aii | 0.8600 | 2.0000 | 2.8293 (14) | 161.00 |
N2A—H2AA···O1Biii | 0.8600 | 1.8900 | 2.7235 (14) | 164.00 |
N1B—H1BC···O1Ai | 0.8600 | 1.8800 | 2.7231 (14) | 165.00 |
N2B—H2BA···O2Biii | 0.8600 | 1.9700 | 2.7412 (14) | 148.00 |
N2B—H2BA···O3Aiv | 0.8600 | 2.4300 | 3.0111 (14) | 125.00 |
C7A—H7AB···O1A | 0.9700 | 2.5300 | 3.0257 (19) | 111.00 |
C11A—H11A···O2Bi | 0.9300 | 2.4900 | 2.9716 (16) | 113.00 |
C11A—H11A···O3Bi | 0.9300 | 2.3500 | 3.2648 (15) | 170.00 |
C11B—H11B···O2Aiv | 0.9300 | 2.3300 | 3.2103 (16) | 159.00 |
C9A—H9AC···O2Ai | 0.9600 | 2.5900 | 3.469 (3) | 152.00 |
C12B—H12B···O3Bi | 0.9300 | 2.3900 | 2.9950 (15) | 122.00 |
C12B—H12B···O4Ai | 0.9300 | 2.4900 | 3.0155 (16) | 116.00 |
C13A—H13A···O2Aiii | 0.9300 | 2.4400 | 3.0167 (16) | 120.00 |
C13A—H13A···O4Aiii | 0.9300 | 2.3900 | 3.2591 (17) | 155.00 |
C13B—H13B···O1Biii | 0.9300 | 2.5800 | 3.2720 (16) | 131.00 |
C7B—H7BA···O2B | 0.9700 | 2.4700 | 3.0613 (16) | 119.00 |
C5A—H5AA···Cg1 | 0.9800 | 2.8300 | 3.5459 (5) | 131.00 |
Symmetry codes: (i) x−1, y, z; (ii) x−1, y, z+1; (iii) −x+2, y−1/2, −z+1; (iv) −x+2, y−1/2, −z. |
Footnotes
‡Additional correspondence author, e-mail: basya@science.upm.edu.my.
Acknowledgements
MBAR, EMO and NSL thank the Malaysian Government and Universiti Putra Malaysia for the Research Universiti Grant Scheme (RUGS 2007) grant No. 91183. MBAR would like to thank Professor Kenneth R. Seddon for the opportunity to conduct this research by SLN at QUILL. HKF and RK thank the Malaysian Government and Universiti Sains Malaysia for the Science Fund grant No. 305/PFIZIK/613312. RK thanks Universiti Sains Malaysia for a post-doctoral research fellowship. HKF also thanks Universiti Sains Malaysia for the Research University Golden Goose grant No. 1001/PFIZIK/811012.
References
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The title compound, (I, Fig. 1), is based on alkyl-imidazole with plant acid as anion (halogen-free). Crystallization of the 1,3-dihydrogenimidazolium camphor-10 -sulfonate having a sulfonate ion as a counter-ion was achieved by a slow evaporation of methanol at ambient temperature. Camphorsulfonate anion was selected due to their low toxicity for biocatalysis applications (Jeremić et al., 2008). The title compound has strong ion-ion interactions between cations and anions, which was attributed to an increase in the van der Waals attraction between the alkyl groups (Fukumoto et al., 2005).
In the title compound (I, Fig. 1), the bond lengths (Allen et al., 1987) and angles are within the normal ranges. There are two intramolecular C—H···O interactions generating six-membered rings with S(6) ring motifs (Bernstein et al., 1995). In the molecule A, the methyl groups are disordered over two positions and refined isotropically with site-ocuppancy ratio of 0.547 (9)/0.453 (9). In the crystal structure, molecules are linked together into 1-D infinite chains along the b axis, and are also linked into 1-D infinite chains along the c axis, thus forming a 2-D network which is parallel to the (100)-plane. The crystal structure is stabilized by intermolecular N—H···O (x 6) and C—H···O (x 9) hydrogen bonds, and weak intermlecular C—H···π interactions (Cg1 is the centroid of the N1B/C11B/N2B/C13B/C12B ring).