The title salt, C
13H
22NO
3+·C
3H
3O
2−, comprises one salbutamol cation and an acrylate anion. The acrylate anion is linked to the salbutamol cation
via an O—H
O and an N—H
O hydrogen bond. The C=C group of the acrylate anion is disordered over two positions, with refined site occupancies of 0.812 (7) and 0.188 (7). The crystal structure is stabilized by N—H
O and O—H
O hydrogen-bonding interactions.
Supporting information
CCDC reference: 1563663
Data collection: APEX2 (Bruker, 2015); cell refinement: SAINT (Bruker, 2015); data reduction: SAINT (Bruker, 2015); program(s) used to solve structure: SHELXT (Sheldrick, 2015a); program(s) used to refine structure: SHELXL2014 (Sheldrick, 2015b); molecular graphics: OLEX2 (Dolomanov et al., 2009); software used to prepare material for publication: OLEX2 (Dolomanov et al., 2009).
rac-
tert-Butyl{2-hydroxy-2-[4-hydroxy-3-(hydroxymethyl)phenyl]ethyl}azanium acrylate
top
Crystal data top
C13H22NO3+·C3H3O2− | F(000) = 672 |
Mr = 311.37 | Dx = 1.248 Mg m−3 |
Monoclinic, P21/c | Mo Kα radiation, λ = 0.71073 Å |
a = 9.5304 (4) Å | Cell parameters from 9984 reflections |
b = 11.9927 (5) Å | θ = 2.7–27.5° |
c = 14.5120 (7) Å | µ = 0.09 mm−1 |
β = 91.815 (2)° | T = 295 K |
V = 1657.82 (13) Å3 | Block, colourless |
Z = 4 | 0.4 × 0.3 × 0.2 mm |
Data collection top
CCD area detector diffractometer | 3468 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.023 |
phi and ω scans | θmax = 27.6°, θmin = 3.3° |
Absorption correction: multi-scan (SADABS; Bruker, 2015) | h = −12→12 |
Tmin = 0.719, Tmax = 0.746 | k = −15→15 |
39441 measured reflections | l = −18→18 |
3825 independent reflections | |
Refinement top
Refinement on F2 | Primary atom site location: dual |
Least-squares matrix: full | Hydrogen site location: inferred from neighbouring sites |
R[F2 > 2σ(F2)] = 0.046 | H-atom parameters constrained |
wR(F2) = 0.125 | w = 1/[σ2(Fo2) + (0.0548P)2 + 0.7417P] where P = (Fo2 + 2Fc2)/3 |
S = 1.04 | (Δ/σ)max < 0.001 |
3825 reflections | Δρmax = 0.39 e Å−3 |
224 parameters | Δρmin = −0.27 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 | Uiso*/Ueq | Occ. (<1) |
O1 | 0.08955 (11) | 0.29361 (8) | 0.85654 (7) | 0.0385 (2) | |
H1 | 0.1603 | 0.2851 | 0.8894 | 0.058* | |
O2 | −0.03078 (10) | −0.00530 (8) | 0.73205 (7) | 0.0388 (2) | |
H2 | −0.0449 | −0.0630 | 0.7028 | 0.058* | |
O3 | 0.32888 (12) | 0.27262 (10) | 0.45673 (7) | 0.0466 (3) | |
H3 | 0.3638 | 0.3271 | 0.4321 | 0.070* | |
O4 | 0.44223 (13) | 0.45453 (9) | 0.37554 (8) | 0.0500 (3) | |
N1 | 0.60151 (11) | 0.33496 (9) | 0.54666 (7) | 0.0299 (2) | |
H1A | 0.5788 | 0.4020 | 0.5678 | 0.036* | |
H1B | 0.5899 | 0.3369 | 0.4856 | 0.036* | |
O5 | 0.61642 (17) | 0.33915 (13) | 0.35229 (10) | 0.0711 (4) | |
C3 | 0.06403 (12) | 0.05912 (10) | 0.68766 (8) | 0.0278 (3) | |
C7 | 0.19586 (13) | 0.22911 (11) | 0.68475 (9) | 0.0295 (3) | |
H7 | 0.2221 | 0.2964 | 0.7121 | 0.035* | |
C2 | 0.10425 (12) | 0.15933 (10) | 0.73002 (8) | 0.0268 (2) | |
C6 | 0.24953 (13) | 0.20124 (11) | 0.59972 (9) | 0.0299 (3) | |
C8 | 0.34961 (13) | 0.28039 (11) | 0.55336 (9) | 0.0322 (3) | |
H8 | 0.3288 | 0.3568 | 0.5727 | 0.039* | |
C4 | 0.11790 (14) | 0.02944 (11) | 0.60353 (9) | 0.0332 (3) | |
H4 | 0.0915 | −0.0377 | 0.5760 | 0.040* | |
C10 | 0.75646 (13) | 0.31554 (12) | 0.56937 (11) | 0.0372 (3) | |
C1 | 0.04384 (15) | 0.18869 (11) | 0.82191 (9) | 0.0336 (3) | |
H1C | −0.0578 | 0.1891 | 0.8155 | 0.040* | |
H1D | 0.0702 | 0.1313 | 0.8663 | 0.040* | |
C5 | 0.21116 (14) | 0.09956 (11) | 0.56033 (9) | 0.0342 (3) | |
H5 | 0.2484 | 0.0784 | 0.5045 | 0.041* | |
C14 | 0.54440 (18) | 0.42130 (13) | 0.32981 (10) | 0.0425 (3) | |
C9 | 0.49975 (14) | 0.25237 (12) | 0.58317 (10) | 0.0354 (3) | |
H9A | 0.5077 | 0.2514 | 0.6500 | 0.042* | |
H9B | 0.5230 | 0.1785 | 0.5611 | 0.042* | |
C13 | 0.83340 (17) | 0.41218 (16) | 0.52486 (14) | 0.0549 (4) | |
H13A | 0.8128 | 0.4124 | 0.4597 | 0.082* | |
H13B | 0.9327 | 0.4036 | 0.5358 | 0.082* | |
H13C | 0.8031 | 0.4813 | 0.5511 | 0.082* | |
C12 | 0.8007 (2) | 0.20572 (16) | 0.52759 (16) | 0.0609 (5) | |
H12A | 0.7579 | 0.1453 | 0.5598 | 0.091* | |
H12B | 0.9009 | 0.1988 | 0.5327 | 0.091* | |
H12C | 0.7711 | 0.2035 | 0.4638 | 0.091* | |
C11 | 0.78183 (17) | 0.31788 (17) | 0.67316 (12) | 0.0541 (4) | |
H11A | 0.7478 | 0.3870 | 0.6973 | 0.081* | |
H11B | 0.8806 | 0.3113 | 0.6872 | 0.081* | |
H11C | 0.7331 | 0.2568 | 0.7006 | 0.081* | |
C15 | 0.5977 (3) | 0.4841 (2) | 0.24830 (16) | 0.0471 (7) | 0.812 (7) |
H15 | 0.6919 | 0.4772 | 0.2345 | 0.057* | 0.812 (7) |
C16 | 0.5186 (4) | 0.5469 (3) | 0.19678 (19) | 0.0701 (9) | 0.812 (7) |
H16A | 0.4241 | 0.5550 | 0.2093 | 0.084* | 0.812 (7) |
H16B | 0.5561 | 0.5842 | 0.1470 | 0.084* | 0.812 (7) |
C15A | 0.5151 (15) | 0.4941 (9) | 0.2405 (6) | 0.053 (3) | 0.188 (7) |
H15A | 0.4254 | 0.5194 | 0.2243 | 0.064* | 0.188 (7) |
C16A | 0.6210 (14) | 0.5165 (11) | 0.1918 (8) | 0.069 (4) | 0.188 (7) |
H16C | 0.7095 | 0.4902 | 0.2096 | 0.083* | 0.188 (7) |
H16D | 0.6094 | 0.5591 | 0.1385 | 0.083* | 0.188 (7) |
Atomic displacement parameters (Å2) top | U11 | U22 | U33 | U12 | U13 | U23 |
O1 | 0.0476 (6) | 0.0325 (5) | 0.0349 (5) | 0.0089 (4) | −0.0042 (4) | −0.0048 (4) |
O2 | 0.0392 (5) | 0.0306 (5) | 0.0473 (6) | −0.0095 (4) | 0.0115 (4) | 0.0010 (4) |
O3 | 0.0444 (6) | 0.0602 (7) | 0.0349 (5) | −0.0197 (5) | −0.0041 (4) | 0.0119 (5) |
O4 | 0.0610 (7) | 0.0387 (6) | 0.0514 (6) | 0.0049 (5) | 0.0162 (5) | 0.0048 (5) |
N1 | 0.0262 (5) | 0.0284 (5) | 0.0351 (5) | −0.0015 (4) | 0.0023 (4) | 0.0035 (4) |
O5 | 0.0847 (10) | 0.0674 (9) | 0.0627 (8) | 0.0246 (8) | 0.0264 (7) | 0.0068 (7) |
C3 | 0.0244 (5) | 0.0245 (5) | 0.0345 (6) | 0.0000 (4) | 0.0020 (4) | 0.0036 (5) |
C7 | 0.0291 (6) | 0.0276 (6) | 0.0317 (6) | −0.0040 (5) | −0.0005 (5) | −0.0014 (5) |
C2 | 0.0255 (5) | 0.0270 (6) | 0.0280 (6) | 0.0019 (4) | −0.0003 (4) | 0.0017 (4) |
C6 | 0.0255 (5) | 0.0315 (6) | 0.0328 (6) | −0.0028 (5) | 0.0015 (4) | 0.0029 (5) |
C8 | 0.0300 (6) | 0.0328 (6) | 0.0338 (6) | −0.0043 (5) | 0.0027 (5) | 0.0038 (5) |
C4 | 0.0361 (6) | 0.0258 (6) | 0.0378 (7) | −0.0017 (5) | 0.0033 (5) | −0.0043 (5) |
C10 | 0.0246 (6) | 0.0370 (7) | 0.0503 (8) | 0.0012 (5) | 0.0041 (5) | −0.0020 (6) |
C1 | 0.0387 (7) | 0.0324 (6) | 0.0299 (6) | 0.0015 (5) | 0.0039 (5) | 0.0014 (5) |
C5 | 0.0359 (6) | 0.0347 (7) | 0.0322 (6) | −0.0006 (5) | 0.0069 (5) | −0.0035 (5) |
C14 | 0.0602 (9) | 0.0360 (7) | 0.0318 (7) | −0.0045 (6) | 0.0101 (6) | −0.0046 (5) |
C9 | 0.0301 (6) | 0.0338 (7) | 0.0421 (7) | −0.0056 (5) | −0.0003 (5) | 0.0092 (5) |
C13 | 0.0365 (8) | 0.0535 (10) | 0.0755 (12) | −0.0114 (7) | 0.0156 (8) | 0.0007 (8) |
C12 | 0.0475 (9) | 0.0467 (9) | 0.0888 (14) | 0.0142 (7) | 0.0091 (9) | −0.0114 (9) |
C11 | 0.0361 (8) | 0.0702 (11) | 0.0554 (10) | 0.0000 (8) | −0.0105 (7) | 0.0037 (8) |
C15 | 0.0484 (14) | 0.0491 (12) | 0.0446 (13) | −0.0059 (11) | 0.0156 (10) | −0.0001 (9) |
C16 | 0.086 (2) | 0.0770 (18) | 0.0488 (14) | 0.0114 (15) | 0.0205 (13) | 0.0207 (14) |
C15A | 0.067 (8) | 0.059 (6) | 0.034 (5) | 0.020 (5) | 0.023 (5) | 0.015 (4) |
C16A | 0.078 (9) | 0.075 (8) | 0.055 (7) | −0.019 (7) | 0.009 (6) | 0.019 (6) |
Geometric parameters (Å, º) top
O1—H1 | 0.8200 | C10—C11 | 1.518 (2) |
O1—C1 | 1.4183 (16) | C1—H1C | 0.9700 |
O2—H2 | 0.8200 | C1—H1D | 0.9700 |
O2—C3 | 1.3656 (14) | C5—H5 | 0.9300 |
O3—H3 | 0.8200 | C14—C15 | 1.504 (3) |
O3—C8 | 1.4130 (16) | C14—C15A | 1.580 (10) |
O4—C14 | 1.2602 (19) | C9—H9A | 0.9700 |
N1—H1A | 0.8900 | C9—H9B | 0.9700 |
N1—H1B | 0.8900 | C13—H13A | 0.9600 |
N1—C10 | 1.5208 (16) | C13—H13B | 0.9600 |
N1—C9 | 1.4950 (16) | C13—H13C | 0.9600 |
O5—C14 | 1.238 (2) | C12—H12A | 0.9600 |
C3—C2 | 1.3979 (17) | C12—H12B | 0.9600 |
C3—C4 | 1.3858 (18) | C12—H12C | 0.9600 |
C7—H7 | 0.9300 | C11—H11A | 0.9600 |
C7—C2 | 1.3895 (17) | C11—H11B | 0.9600 |
C7—C6 | 1.3914 (18) | C11—H11C | 0.9600 |
C2—C1 | 1.5108 (17) | C15—H15 | 0.9300 |
C6—C8 | 1.5179 (17) | C15—C16 | 1.288 (4) |
C6—C5 | 1.3908 (18) | C16—H16A | 0.9300 |
C8—H8 | 0.9800 | C16—H16B | 0.9300 |
C8—C9 | 1.5193 (18) | C15A—H15A | 0.9300 |
C4—H4 | 0.9300 | C15A—C16A | 1.279 (14) |
C4—C5 | 1.3876 (19) | C16A—H16C | 0.9300 |
C10—C13 | 1.526 (2) | C16A—H16D | 0.9300 |
C10—C12 | 1.515 (2) | | |
| | | |
C1—O1—H1 | 109.5 | C4—C5—C6 | 120.62 (12) |
C3—O2—H2 | 109.5 | C4—C5—H5 | 119.7 |
C8—O3—H3 | 109.5 | O4—C14—C15 | 122.80 (17) |
H1A—N1—H1B | 107.2 | O4—C14—C15A | 97.9 (4) |
C10—N1—H1A | 108.0 | O5—C14—O4 | 122.95 (14) |
C10—N1—H1B | 108.0 | O5—C14—C15 | 114.02 (17) |
C9—N1—H1A | 108.0 | O5—C14—C15A | 137.5 (4) |
C9—N1—H1B | 108.0 | N1—C9—C8 | 111.61 (11) |
C9—N1—C10 | 117.27 (10) | N1—C9—H9A | 109.3 |
O2—C3—C2 | 117.08 (11) | N1—C9—H9B | 109.3 |
O2—C3—C4 | 122.65 (11) | C8—C9—H9A | 109.3 |
C4—C3—C2 | 120.27 (11) | C8—C9—H9B | 109.3 |
C2—C7—H7 | 119.0 | H9A—C9—H9B | 108.0 |
C2—C7—C6 | 121.92 (11) | C10—C13—H13A | 109.5 |
C6—C7—H7 | 119.0 | C10—C13—H13B | 109.5 |
C3—C2—C1 | 118.80 (11) | C10—C13—H13C | 109.5 |
C7—C2—C3 | 118.53 (11) | H13A—C13—H13B | 109.5 |
C7—C2—C1 | 122.66 (11) | H13A—C13—H13C | 109.5 |
C7—C6—C8 | 119.78 (11) | H13B—C13—H13C | 109.5 |
C5—C6—C7 | 118.42 (11) | C10—C12—H12A | 109.5 |
C5—C6—C8 | 121.79 (11) | C10—C12—H12B | 109.5 |
O3—C8—C6 | 109.18 (10) | C10—C12—H12C | 109.5 |
O3—C8—H8 | 108.8 | H12A—C12—H12B | 109.5 |
O3—C8—C9 | 111.64 (11) | H12A—C12—H12C | 109.5 |
C6—C8—H8 | 108.8 | H12B—C12—H12C | 109.5 |
C6—C8—C9 | 109.56 (11) | C10—C11—H11A | 109.5 |
C9—C8—H8 | 108.8 | C10—C11—H11B | 109.5 |
C3—C4—H4 | 119.9 | C10—C11—H11C | 109.5 |
C3—C4—C5 | 120.19 (12) | H11A—C11—H11B | 109.5 |
C5—C4—H4 | 119.9 | H11A—C11—H11C | 109.5 |
N1—C10—C13 | 105.57 (12) | H11B—C11—H11C | 109.5 |
C12—C10—N1 | 109.07 (12) | C14—C15—H15 | 118.5 |
C12—C10—C13 | 110.33 (14) | C16—C15—C14 | 122.9 (3) |
C12—C10—C11 | 112.05 (15) | C16—C15—H15 | 118.5 |
C11—C10—N1 | 109.59 (11) | C15—C16—H16A | 120.0 |
C11—C10—C13 | 110.03 (14) | C15—C16—H16B | 120.0 |
O1—C1—C2 | 113.46 (11) | H16A—C16—H16B | 120.0 |
O1—C1—H1C | 108.9 | C14—C15A—H15A | 121.7 |
O1—C1—H1D | 108.9 | C16A—C15A—C14 | 116.6 (12) |
C2—C1—H1C | 108.9 | C16A—C15A—H15A | 121.7 |
C2—C1—H1D | 108.9 | C15A—C16A—H16C | 120.0 |
H1C—C1—H1D | 107.7 | C15A—C16A—H16D | 120.0 |
C6—C5—H5 | 119.7 | H16C—C16A—H16D | 120.0 |
Hydrogen-bond geometry (Å, º) top
D—H···A | D—H | H···A | D···A | D—H···A |
O1—H1···O3i | 0.82 | 1.98 | 2.7817 (14) | 166 |
O2—H2···O1ii | 0.82 | 1.96 | 2.7816 (14) | 174 |
O3—H3···O4 | 0.82 | 1.90 | 2.7194 (15) | 179 |
N1—H1A···O4iii | 0.89 | 1.92 | 2.8022 (16) | 171 |
N1—H1B···O5 | 0.89 | 1.96 | 2.8292 (18) | 166 |
Symmetry codes: (i) x, −y+1/2, z+1/2; (ii) −x, y−1/2, −z+3/2; (iii) −x+1, −y+1, −z+1. |