organic compounds
(2,4,6-Trimethylphenyl){2-[N-(2,4,6-trimethylphenyl)formamido]ethyl}ammonium chloride
aSchool of Chemistry, University of KwaZulu-Natal, Westville Campus, Private Bag X54001, Durban 4000, South Africa
*Correspondence e-mail: bala@ukzn.ac.za
In the title salt, C21H29N2O+·Cl−, the benzene rings form a dihedral angle of 6.13 (1)°. In the crystal, N—H⋯Cl hydrogen bonds link the cations and anions into chains extending along the c axis.
Experimental
Crystal data
|
Data collection
|
Refinement
|
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.
Supporting information
10.1107/S1600536812044595/xu5637sup1.cif
contains datablocks I, global. DOI:Structure factors: contains datablock I. DOI: 10.1107/S1600536812044595/xu5637Isup2.hkl
A mixture of 1,3–bis(2,4,6-trimethyl phenyl)imidazolinium chloride (0.101 g, 0.29 mmol) and potassium tert-butoxide (0.039 g, 0.35 mmol) were dissolved in 20 ml of tetrahydrofuran and stirred at room temperature for 30 min. After evaporating the solvent, the free carbene was extracted in warm toluene (2 x 20 ml). FeCl2 (0.037 g, 0.29 mmol) was added to the toluene solution and refluxed for 24 h at 90 °C. Removal of the solvent gave a residue that was purified by recrystallization from CH2Cl2/hexane to yield orange crystals of (I). Yield: 0.05 g, 51%; m.p. 180 °C.
H-atoms were refined using a riding model, with C—H = 0.95 Å and Uiso(H) = 1.2Ueq(C) for aromatic and C—H = 0.98 Å and Uiso(H) = 1.5Ueq(C) for CH3. The amino H atoms were placed in calculated positions with N—H = 0.92 Å and refined in a riding mode with Uiso(H) = 1.2Ueq(N).
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).C21H29N2O+·Cl− | Z = 2 |
Mr = 360.91 | F(000) = 388 |
Triclinic, P1 | Dx = 1.191 Mg m−3 |
Hall symbol: -P 1 | Mo Kα radiation, λ = 0.71073 Å |
a = 8.2516 (2) Å | Cell parameters from 3132 reflections |
b = 8.8822 (2) Å | θ = 2.5–24.0° |
c = 14.7524 (4) Å | µ = 0.20 mm−1 |
α = 74.857 (2)° | T = 173 K |
β = 86.315 (2)° | Block, colourless |
γ = 74.635 (2)° | 0.36 × 0.21 × 0.11 mm |
V = 1006.38 (5) Å3 |
Bruker APEXII CCD diffractometer | 2975 reflections with I > 2σ(I) |
Radiation source: fine-focus sealed tube | Rint = 0.062 |
Graphite monochromator | θmax = 28.0°, θmin = 1.4° |
ϕ and ω scans | h = −10→10 |
19610 measured reflections | k = −11→11 |
4853 independent reflections | l = −19→19 |
Refinement on F2 | Primary atom site location: structure-invariant direct methods |
Least-squares matrix: full | Secondary atom site location: difference Fourier map |
R[F2 > 2σ(F2)] = 0.044 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.107 | H-atom parameters constrained |
S = 0.90 | w = 1/[σ2(Fo2) + (0.0478P)2] where P = (Fo2 + 2Fc2)/3 |
4853 reflections | (Δ/σ)max = 0.001 |
232 parameters | Δρmax = 0.31 e Å−3 |
0 restraints | Δρmin = −0.25 e Å−3 |
C21H29N2O+·Cl− | γ = 74.635 (2)° |
Mr = 360.91 | V = 1006.38 (5) Å3 |
Triclinic, P1 | Z = 2 |
a = 8.2516 (2) Å | Mo Kα radiation |
b = 8.8822 (2) Å | µ = 0.20 mm−1 |
c = 14.7524 (4) Å | T = 173 K |
α = 74.857 (2)° | 0.36 × 0.21 × 0.11 mm |
β = 86.315 (2)° |
Bruker APEXII CCD diffractometer | 2975 reflections with I > 2σ(I) |
19610 measured reflections | Rint = 0.062 |
4853 independent reflections |
R[F2 > 2σ(F2)] = 0.044 | 0 restraints |
wR(F2) = 0.107 | H-atom parameters constrained |
S = 0.90 | Δρmax = 0.31 e Å−3 |
4853 reflections | Δρmin = −0.25 e Å−3 |
232 parameters |
Experimental. IR (ATR cm-1): 2918, 2718, 2607, 1669, 1568, 1482, 1446, 1381, 1345, 1306, 1285, 1207, 1193, 1033, 850, 781, 705, 577, 477, 425; δH (400 MHz, CDCl3): 1.60 (6H, s, CH3), 2.16 (12H, m, CH3), 2.58 (3H, s, NH2), 3.76 (2H, s, NCH2NCHO), 6.83 (3H, s, ArH), 6.88 (2H, s, ArH) and 7.89 p.p.m. (1H, s, NCHO); δC (100 MHz, CDCl3): 18.09 (C6H2(CH3)3), 19.35 (C6H2(CH3)3), 21.15 (C6H2(CH3)3), 23.17 (C6H2(CH3)3), 51.12 (NHCH2), 52.08 (NCH2), 128.27, 130.18, 134.72, 135.91, 138.54, 140.21, 145.23 and 160.28 p.p.m. (NCHO); HRMS (ESI), Found, 325.22737 (M+ - Cl-) Calculated for C21H29N2O 325.22799 (M+ - Cl-). |
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 | ||
C1 | −0.0762 (2) | 0.8248 (2) | 0.13320 (12) | 0.0263 (4) | |
C2 | −0.0175 (2) | 0.9590 (2) | 0.13117 (12) | 0.0298 (4) | |
C3 | −0.1346 (2) | 1.1060 (2) | 0.12548 (13) | 0.0347 (5) | |
H3 | −0.0958 | 1.1971 | 0.1266 | 0.042* | |
C4 | −0.3055 (2) | 1.1251 (2) | 0.11826 (13) | 0.0365 (5) | |
C5 | −0.3594 (2) | 0.9905 (2) | 0.11714 (13) | 0.0373 (5) | |
H5 | −0.4761 | 1.0021 | 0.1104 | 0.045* | |
C6 | −0.2486 (2) | 0.8385 (2) | 0.12561 (12) | 0.0318 (4) | |
C7 | 0.1675 (2) | 0.9497 (2) | 0.13254 (14) | 0.0390 (5) | |
H7A | 0.2107 | 0.9029 | 0.1969 | 0.058* | |
H7B | 0.1844 | 1.0584 | 0.1096 | 0.058* | |
H7C | 0.2277 | 0.8817 | 0.0920 | 0.058* | |
C8 | −0.4291 (3) | 1.2871 (3) | 0.11207 (17) | 0.0573 (6) | |
H8A | −0.4089 | 1.3296 | 0.1641 | 0.086* | |
H8B | −0.5439 | 1.2744 | 0.1159 | 0.086* | |
H8C | −0.4145 | 1.3622 | 0.0522 | 0.086* | |
C9 | −0.3162 (2) | 0.6959 (2) | 0.12768 (15) | 0.0441 (5) | |
H9A | −0.2934 | 0.6669 | 0.0676 | 0.066* | |
H9B | −0.4378 | 0.7239 | 0.1383 | 0.066* | |
H9C | −0.2616 | 0.6041 | 0.1786 | 0.066* | |
C10 | 0.0609 (2) | 0.5899 (2) | 0.07631 (14) | 0.0392 (5) | |
H10 | 0.0013 | 0.6435 | 0.0190 | 0.047* | |
C11 | 0.1348 (2) | 0.5881 (2) | 0.23205 (12) | 0.0288 (4) | |
H11A | 0.1508 | 0.6696 | 0.2630 | 0.035* | |
H11B | 0.2471 | 0.5234 | 0.2188 | 0.035* | |
C12 | 0.0402 (2) | 0.4789 (2) | 0.29708 (12) | 0.0277 (4) | |
H12A | −0.0680 | 0.5452 | 0.3143 | 0.033* | |
H12B | 0.0153 | 0.4042 | 0.2638 | 0.033* | |
C13 | 0.2789 (2) | 0.2444 (2) | 0.37526 (12) | 0.0249 (4) | |
C14 | 0.2386 (2) | 0.1044 (2) | 0.36930 (12) | 0.0265 (4) | |
C15 | 0.3711 (2) | −0.0292 (2) | 0.36709 (12) | 0.0320 (4) | |
H15 | 0.3467 | −0.1262 | 0.3634 | 0.038* | |
C16 | 0.5376 (2) | −0.0257 (2) | 0.37002 (12) | 0.0328 (4) | |
C17 | 0.5706 (2) | 0.1165 (2) | 0.37419 (13) | 0.0345 (5) | |
H17 | 0.6843 | 0.1205 | 0.3750 | 0.041* | |
C18 | 0.4440 (2) | 0.2546 (2) | 0.37721 (12) | 0.0280 (4) | |
C19 | 0.0599 (2) | 0.0917 (2) | 0.36649 (14) | 0.0345 (5) | |
H19A | −0.0098 | 0.1503 | 0.4090 | 0.052* | |
H19B | 0.0581 | −0.0221 | 0.3863 | 0.052* | |
H19C | 0.0155 | 0.1386 | 0.3024 | 0.052* | |
C20 | 0.6787 (2) | −0.1744 (2) | 0.36982 (15) | 0.0471 (6) | |
H20A | 0.6388 | −0.2712 | 0.3968 | 0.071* | |
H20B | 0.7730 | −0.1756 | 0.4074 | 0.071* | |
H20C | 0.7157 | −0.1727 | 0.3052 | 0.071* | |
C21 | 0.4916 (2) | 0.4051 (2) | 0.38237 (15) | 0.0409 (5) | |
H21A | 0.6129 | 0.3795 | 0.3934 | 0.061* | |
H21B | 0.4309 | 0.4457 | 0.4340 | 0.061* | |
H21C | 0.4620 | 0.4877 | 0.3231 | 0.061* | |
N1 | 0.04243 (17) | 0.66963 (18) | 0.14387 (10) | 0.0289 (3) | |
N2 | 0.13837 (16) | 0.38311 (16) | 0.38442 (10) | 0.0246 (3) | |
H2A | 0.1811 | 0.4518 | 0.4072 | 0.030* | |
H2B | 0.0652 | 0.3452 | 0.4287 | 0.030* | |
O1 | 0.14983 (17) | 0.45239 (18) | 0.08378 (10) | 0.0544 (4) | |
Cl1 | 0.13717 (5) | 0.66160 (5) | 0.47043 (3) | 0.03312 (14) |
U11 | U22 | U33 | U12 | U13 | U23 | |
C1 | 0.0249 (9) | 0.0308 (10) | 0.0200 (9) | −0.0033 (8) | −0.0015 (7) | −0.0046 (8) |
C2 | 0.0297 (10) | 0.0356 (11) | 0.0228 (9) | −0.0091 (9) | −0.0013 (8) | −0.0041 (8) |
C3 | 0.0427 (11) | 0.0315 (11) | 0.0277 (10) | −0.0080 (9) | −0.0031 (9) | −0.0043 (9) |
C4 | 0.0357 (11) | 0.0368 (12) | 0.0290 (10) | 0.0015 (9) | −0.0019 (9) | −0.0052 (9) |
C5 | 0.0236 (9) | 0.0494 (13) | 0.0331 (11) | −0.0026 (9) | −0.0023 (8) | −0.0069 (10) |
C6 | 0.0280 (10) | 0.0399 (12) | 0.0261 (10) | −0.0075 (9) | −0.0019 (8) | −0.0065 (9) |
C7 | 0.0321 (10) | 0.0436 (12) | 0.0413 (12) | −0.0132 (9) | −0.0015 (9) | −0.0071 (10) |
C8 | 0.0571 (14) | 0.0446 (14) | 0.0557 (15) | 0.0123 (11) | −0.0079 (12) | −0.0117 (12) |
C9 | 0.0331 (11) | 0.0495 (13) | 0.0516 (14) | −0.0140 (10) | −0.0051 (10) | −0.0115 (11) |
C10 | 0.0345 (11) | 0.0473 (13) | 0.0331 (11) | 0.0000 (10) | −0.0053 (9) | −0.0152 (10) |
C11 | 0.0262 (9) | 0.0323 (10) | 0.0252 (9) | −0.0033 (8) | −0.0053 (7) | −0.0056 (8) |
C12 | 0.0225 (9) | 0.0274 (10) | 0.0295 (10) | −0.0014 (8) | −0.0067 (7) | −0.0044 (8) |
C13 | 0.0222 (9) | 0.0263 (10) | 0.0226 (9) | 0.0004 (7) | −0.0028 (7) | −0.0058 (8) |
C14 | 0.0265 (9) | 0.0268 (10) | 0.0232 (9) | −0.0025 (8) | −0.0016 (7) | −0.0052 (8) |
C15 | 0.0372 (11) | 0.0276 (10) | 0.0275 (10) | −0.0028 (8) | 0.0009 (8) | −0.0067 (8) |
C16 | 0.0313 (10) | 0.0345 (11) | 0.0242 (10) | 0.0044 (9) | 0.0000 (8) | −0.0060 (8) |
C17 | 0.0208 (9) | 0.0479 (12) | 0.0291 (10) | −0.0014 (9) | 0.0001 (8) | −0.0077 (9) |
C18 | 0.0232 (9) | 0.0363 (11) | 0.0234 (9) | −0.0056 (8) | −0.0026 (7) | −0.0074 (8) |
C19 | 0.0322 (10) | 0.0308 (11) | 0.0443 (12) | −0.0095 (9) | −0.0002 (9) | −0.0143 (9) |
C20 | 0.0418 (12) | 0.0468 (13) | 0.0361 (12) | 0.0127 (10) | 0.0024 (9) | −0.0070 (10) |
C21 | 0.0272 (10) | 0.0490 (13) | 0.0514 (13) | −0.0133 (9) | −0.0024 (9) | −0.0172 (11) |
N1 | 0.0295 (8) | 0.0312 (9) | 0.0227 (8) | −0.0015 (7) | −0.0042 (6) | −0.0065 (7) |
N2 | 0.0225 (7) | 0.0259 (8) | 0.0264 (8) | −0.0065 (6) | 0.0002 (6) | −0.0079 (6) |
O1 | 0.0514 (9) | 0.0540 (10) | 0.0525 (10) | 0.0147 (8) | −0.0150 (8) | −0.0295 (8) |
Cl1 | 0.0312 (3) | 0.0314 (3) | 0.0414 (3) | −0.0118 (2) | 0.0066 (2) | −0.0148 (2) |
C1—C2 | 1.394 (2) | C11—H11B | 0.9900 |
C1—C6 | 1.404 (2) | C12—N2 | 1.495 (2) |
C1—N1 | 1.440 (2) | C12—H12A | 0.9900 |
C2—C3 | 1.389 (2) | C12—H12B | 0.9900 |
C2—C7 | 1.508 (2) | C13—C18 | 1.392 (2) |
C3—C4 | 1.383 (3) | C13—C14 | 1.394 (2) |
C3—H3 | 0.9500 | C13—N2 | 1.4802 (19) |
C4—C5 | 1.385 (3) | C14—C15 | 1.391 (2) |
C4—C8 | 1.511 (3) | C14—C19 | 1.513 (2) |
C5—C6 | 1.396 (2) | C15—C16 | 1.386 (2) |
C5—H5 | 0.9500 | C15—H15 | 0.9500 |
C6—C9 | 1.506 (3) | C16—C17 | 1.378 (3) |
C7—H7A | 0.9800 | C16—C20 | 1.512 (2) |
C7—H7B | 0.9800 | C17—C18 | 1.393 (2) |
C7—H7C | 0.9800 | C17—H17 | 0.9500 |
C8—H8A | 0.9800 | C18—C21 | 1.511 (2) |
C8—H8B | 0.9800 | C19—H19A | 0.9800 |
C8—H8C | 0.9800 | C19—H19B | 0.9800 |
C9—H9A | 0.9800 | C19—H19C | 0.9800 |
C9—H9B | 0.9800 | C20—H20A | 0.9800 |
C9—H9C | 0.9800 | C20—H20B | 0.9800 |
C10—O1 | 1.227 (2) | C20—H20C | 0.9800 |
C10—N1 | 1.345 (2) | C21—H21A | 0.9800 |
C10—H10 | 0.9500 | C21—H21B | 0.9800 |
C11—N1 | 1.463 (2) | C21—H21C | 0.9800 |
C11—C12 | 1.513 (2) | N2—H2A | 0.9200 |
C11—H11A | 0.9900 | N2—H2B | 0.9200 |
C2—C1—C6 | 121.13 (16) | N2—C12—H12B | 109.2 |
C2—C1—N1 | 119.19 (15) | C11—C12—H12B | 109.2 |
C6—C1—N1 | 119.69 (15) | H12A—C12—H12B | 107.9 |
C3—C2—C1 | 118.23 (16) | C18—C13—C14 | 122.59 (15) |
C3—C2—C7 | 119.68 (16) | C18—C13—N2 | 119.86 (15) |
C1—C2—C7 | 122.08 (16) | C14—C13—N2 | 117.49 (14) |
C4—C3—C2 | 122.63 (18) | C15—C14—C13 | 117.36 (15) |
C4—C3—H3 | 118.7 | C15—C14—C19 | 119.38 (16) |
C2—C3—H3 | 118.7 | C13—C14—C19 | 123.25 (15) |
C3—C4—C5 | 117.69 (17) | C16—C15—C14 | 122.21 (17) |
C3—C4—C8 | 121.08 (19) | C16—C15—H15 | 118.9 |
C5—C4—C8 | 121.24 (18) | C14—C15—H15 | 118.9 |
C4—C5—C6 | 122.44 (17) | C17—C16—C15 | 118.06 (16) |
C4—C5—H5 | 118.8 | C17—C16—C20 | 121.05 (17) |
C6—C5—H5 | 118.8 | C15—C16—C20 | 120.88 (18) |
C5—C6—C1 | 117.82 (17) | C16—C17—C18 | 122.75 (17) |
C5—C6—C9 | 119.69 (16) | C16—C17—H17 | 118.6 |
C1—C6—C9 | 122.49 (17) | C18—C17—H17 | 118.6 |
C2—C7—H7A | 109.5 | C13—C18—C17 | 117.00 (16) |
C2—C7—H7B | 109.5 | C13—C18—C21 | 123.79 (16) |
H7A—C7—H7B | 109.5 | C17—C18—C21 | 119.21 (16) |
C2—C7—H7C | 109.5 | C14—C19—H19A | 109.5 |
H7A—C7—H7C | 109.5 | C14—C19—H19B | 109.5 |
H7B—C7—H7C | 109.5 | H19A—C19—H19B | 109.5 |
C4—C8—H8A | 109.5 | C14—C19—H19C | 109.5 |
C4—C8—H8B | 109.5 | H19A—C19—H19C | 109.5 |
H8A—C8—H8B | 109.5 | H19B—C19—H19C | 109.5 |
C4—C8—H8C | 109.5 | C16—C20—H20A | 109.5 |
H8A—C8—H8C | 109.5 | C16—C20—H20B | 109.5 |
H8B—C8—H8C | 109.5 | H20A—C20—H20B | 109.5 |
C6—C9—H9A | 109.5 | C16—C20—H20C | 109.5 |
C6—C9—H9B | 109.5 | H20A—C20—H20C | 109.5 |
H9A—C9—H9B | 109.5 | H20B—C20—H20C | 109.5 |
C6—C9—H9C | 109.5 | C18—C21—H21A | 109.5 |
H9A—C9—H9C | 109.5 | C18—C21—H21B | 109.5 |
H9B—C9—H9C | 109.5 | H21A—C21—H21B | 109.5 |
O1—C10—N1 | 124.35 (18) | C18—C21—H21C | 109.5 |
O1—C10—H10 | 117.8 | H21A—C21—H21C | 109.5 |
N1—C10—H10 | 117.8 | H21B—C21—H21C | 109.5 |
N1—C11—C12 | 110.66 (14) | C10—N1—C1 | 121.01 (15) |
N1—C11—H11A | 109.5 | C10—N1—C11 | 118.12 (15) |
C12—C11—H11A | 109.5 | C1—N1—C11 | 120.64 (14) |
N1—C11—H11B | 109.5 | C13—N2—C12 | 116.63 (13) |
C12—C11—H11B | 109.5 | C13—N2—H2A | 108.1 |
H11A—C11—H11B | 108.1 | C12—N2—H2A | 108.1 |
N2—C12—C11 | 111.89 (13) | C13—N2—H2B | 108.1 |
N2—C12—H12A | 109.2 | C12—N2—H2B | 108.1 |
C11—C12—H12A | 109.2 | H2A—N2—H2B | 107.3 |
C6—C1—C2—C3 | 2.7 (3) | C19—C14—C15—C16 | −179.61 (17) |
N1—C1—C2—C3 | −176.89 (16) | C14—C15—C16—C17 | −0.8 (3) |
C6—C1—C2—C7 | −175.73 (17) | C14—C15—C16—C20 | 178.54 (17) |
N1—C1—C2—C7 | 4.6 (3) | C15—C16—C17—C18 | 1.2 (3) |
C1—C2—C3—C4 | −2.5 (3) | C20—C16—C17—C18 | −178.12 (17) |
C7—C2—C3—C4 | 176.02 (17) | C14—C13—C18—C17 | −0.8 (3) |
C2—C3—C4—C5 | 0.3 (3) | N2—C13—C18—C17 | 176.08 (15) |
C2—C3—C4—C8 | −179.90 (18) | C14—C13—C18—C21 | 179.17 (17) |
C3—C4—C5—C6 | 1.8 (3) | N2—C13—C18—C21 | −3.9 (3) |
C8—C4—C5—C6 | −178.02 (19) | C16—C17—C18—C13 | −0.4 (3) |
C4—C5—C6—C1 | −1.6 (3) | C16—C17—C18—C21 | 179.60 (17) |
C4—C5—C6—C9 | 177.59 (18) | O1—C10—N1—C1 | −174.15 (17) |
C2—C1—C6—C5 | −0.8 (3) | O1—C10—N1—C11 | 0.4 (3) |
N1—C1—C6—C5 | 178.83 (15) | C2—C1—N1—C10 | −117.52 (19) |
C2—C1—C6—C9 | −179.92 (17) | C6—C1—N1—C10 | 62.9 (2) |
N1—C1—C6—C9 | −0.3 (3) | C2—C1—N1—C11 | 68.1 (2) |
N1—C11—C12—N2 | 175.09 (13) | C6—C1—N1—C11 | −111.52 (18) |
C18—C13—C14—C15 | 1.2 (3) | C12—C11—N1—C10 | −83.4 (2) |
N2—C13—C14—C15 | −175.77 (15) | C12—C11—N1—C1 | 91.09 (18) |
C18—C13—C14—C19 | −179.60 (17) | C18—C13—N2—C12 | 106.18 (18) |
N2—C13—C14—C19 | 3.4 (2) | C14—C13—N2—C12 | −76.74 (19) |
C13—C14—C15—C16 | −0.4 (3) | C11—C12—N2—C13 | −75.89 (18) |
D—H···A | D—H | H···A | D···A | D—H···A |
N2—H2A···Cl1 | 0.92 | 2.23 | 3.0585 (14) | 149 |
N2—H2B···Cl1i | 0.92 | 2.17 | 3.0531 (14) | 161 |
Symmetry code: (i) −x, −y+1, −z+1. |
Experimental details
Crystal data | |
Chemical formula | C21H29N2O+·Cl− |
Mr | 360.91 |
Crystal system, space group | Triclinic, P1 |
Temperature (K) | 173 |
a, b, c (Å) | 8.2516 (2), 8.8822 (2), 14.7524 (4) |
α, β, γ (°) | 74.857 (2), 86.315 (2), 74.635 (2) |
V (Å3) | 1006.38 (5) |
Z | 2 |
Radiation type | Mo Kα |
µ (mm−1) | 0.20 |
Crystal size (mm) | 0.36 × 0.21 × 0.11 |
Data collection | |
Diffractometer | Bruker APEXII CCD diffractometer |
Absorption correction | – |
No. of measured, independent and observed [I > 2σ(I)] reflections | 19610, 4853, 2975 |
Rint | 0.062 |
(sin θ/λ)max (Å−1) | 0.661 |
Refinement | |
R[F2 > 2σ(F2)], wR(F2), S | 0.044, 0.107, 0.90 |
No. of reflections | 4853 |
No. of parameters | 232 |
H-atom treatment | H-atom parameters constrained |
Δρmax, Δρmin (e Å−3) | 0.31, −0.25 |
Computer programs: APEX2 (Bruker, 2005), SAINT (Bruker, 2005), SHELXTL (Sheldrick, 2008).
D—H···A | D—H | H···A | D···A | D—H···A |
N2—H2A···Cl1 | 0.92 | 2.23 | 3.0585 (14) | 149.2 |
N2—H2B···Cl1i | 0.92 | 2.17 | 3.0531 (14) | 161.4 |
Symmetry code: (i) −x, −y+1, −z+1. |
Acknowledgements
We thank Dr Manuel Fernandes for the data collection and the University of KwaZulu-Natal for financial support.
References
Bruker (2005). APEX2 and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA. Google Scholar
Denk, M. K., Rodezno, J. M., Gupta, S. & Lough, A. J. (2001). J. Organomet. Chem. 617, 242–253. Web of Science CSD CrossRef Google Scholar
Kocher, C. & Hermann, W. A. (1997). J. Organomet. Chem. 532, 261–265. Google Scholar
Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. Web of Science CrossRef CAS IUCr Journals Google Scholar
This is an open-access article distributed under the terms of the Creative Commons Attribution (CC-BY) Licence, which permits unrestricted use, distribution, and reproduction in any medium, provided the original authors and source are cited.
The title compound was isolated from the hydrolysis of an imidazolium based salt in a ring opening reaction. Stable N-heterocyclic carbene ligands are often prepared from imidazolium based salt precursors. However the reaction must be conducted under strict anaerobic conditions using Schlenk techniques, otherwise attack by moisture will lead to the isolation of products such as (I).
In (I) (Fig.1), the planes of the two phenyl rings (mean: C1–C6 and mean: C13–C18) form a dihedral angle of 6.13 (1)°. In the crystal, intermolecular N—H···Cl hydrogen bonds (Table 1) link the molecules into chains extending along the crystallographic c axis with a separation of 2.17–2.23 Å (Fig. 2).