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The title salt, C13H22NO3+·C3H3O2, 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

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S2414314617011890/bt4060sup1.cif
Contains datablock I

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S2414314617011890/bt4060Isup2.hkl
Contains datablock I

cml

Chemical Markup Language (CML) file https://doi.org/10.1107/S2414314617011890/bt4060Isup3.cml
Supplementary material

CCDC reference: 1563663

Computing details top

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+·C3H3O2F(000) = 672
Mr = 311.37Dx = 1.248 Mg m3
Monoclinic, P21/cMo Kα radiation, λ = 0.71073 Å
a = 9.5304 (4) ÅCell parameters from 9984 reflections
b = 11.9927 (5) Åθ = 2.7–27.5°
c = 14.5120 (7) ŵ = 0.09 mm1
β = 91.815 (2)°T = 295 K
V = 1657.82 (13) Å3Block, colourless
Z = 40.4 × 0.3 × 0.2 mm
Data collection top
CCD area detector
diffractometer
3468 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.023
phi and ω scansθmax = 27.6°, θmin = 3.3°
Absorption correction: multi-scan
(SADABS; Bruker, 2015)
h = 1212
Tmin = 0.719, Tmax = 0.746k = 1515
39441 measured reflectionsl = 1818
3825 independent reflections
Refinement top
Refinement on F2Primary atom site location: dual
Least-squares matrix: fullHydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.046H-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 reflectionsΔρmax = 0.39 e Å3
224 parametersΔρmin = 0.27 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)
O10.08955 (11)0.29361 (8)0.85654 (7)0.0385 (2)
H10.16030.28510.88940.058*
O20.03078 (10)0.00530 (8)0.73205 (7)0.0388 (2)
H20.04490.06300.70280.058*
O30.32888 (12)0.27262 (10)0.45673 (7)0.0466 (3)
H30.36380.32710.43210.070*
O40.44223 (13)0.45453 (9)0.37554 (8)0.0500 (3)
N10.60151 (11)0.33496 (9)0.54666 (7)0.0299 (2)
H1A0.57880.40200.56780.036*
H1B0.58990.33690.48560.036*
O50.61642 (17)0.33915 (13)0.35229 (10)0.0711 (4)
C30.06403 (12)0.05912 (10)0.68766 (8)0.0278 (3)
C70.19586 (13)0.22911 (11)0.68475 (9)0.0295 (3)
H70.22210.29640.71210.035*
C20.10425 (12)0.15933 (10)0.73002 (8)0.0268 (2)
C60.24953 (13)0.20124 (11)0.59972 (9)0.0299 (3)
C80.34961 (13)0.28039 (11)0.55336 (9)0.0322 (3)
H80.32880.35680.57270.039*
C40.11790 (14)0.02944 (11)0.60353 (9)0.0332 (3)
H40.09150.03770.57600.040*
C100.75646 (13)0.31554 (12)0.56937 (11)0.0372 (3)
C10.04384 (15)0.18869 (11)0.82191 (9)0.0336 (3)
H1C0.05780.18910.81550.040*
H1D0.07020.13130.86630.040*
C50.21116 (14)0.09956 (11)0.56033 (9)0.0342 (3)
H50.24840.07840.50450.041*
C140.54440 (18)0.42130 (13)0.32981 (10)0.0425 (3)
C90.49975 (14)0.25237 (12)0.58317 (10)0.0354 (3)
H9A0.50770.25140.65000.042*
H9B0.52300.17850.56110.042*
C130.83340 (17)0.41218 (16)0.52486 (14)0.0549 (4)
H13A0.81280.41240.45970.082*
H13B0.93270.40360.53580.082*
H13C0.80310.48130.55110.082*
C120.8007 (2)0.20572 (16)0.52759 (16)0.0609 (5)
H12A0.75790.14530.55980.091*
H12B0.90090.19880.53270.091*
H12C0.77110.20350.46380.091*
C110.78183 (17)0.31788 (17)0.67316 (12)0.0541 (4)
H11A0.74780.38700.69730.081*
H11B0.88060.31130.68720.081*
H11C0.73310.25680.70060.081*
C150.5977 (3)0.4841 (2)0.24830 (16)0.0471 (7)0.812 (7)
H150.69190.47720.23450.057*0.812 (7)
C160.5186 (4)0.5469 (3)0.19678 (19)0.0701 (9)0.812 (7)
H16A0.42410.55500.20930.084*0.812 (7)
H16B0.55610.58420.14700.084*0.812 (7)
C15A0.5151 (15)0.4941 (9)0.2405 (6)0.053 (3)0.188 (7)
H15A0.42540.51940.22430.064*0.188 (7)
C16A0.6210 (14)0.5165 (11)0.1918 (8)0.069 (4)0.188 (7)
H16C0.70950.49020.20960.083*0.188 (7)
H16D0.60940.55910.13850.083*0.188 (7)
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
O10.0476 (6)0.0325 (5)0.0349 (5)0.0089 (4)0.0042 (4)0.0048 (4)
O20.0392 (5)0.0306 (5)0.0473 (6)0.0095 (4)0.0115 (4)0.0010 (4)
O30.0444 (6)0.0602 (7)0.0349 (5)0.0197 (5)0.0041 (4)0.0119 (5)
O40.0610 (7)0.0387 (6)0.0514 (6)0.0049 (5)0.0162 (5)0.0048 (5)
N10.0262 (5)0.0284 (5)0.0351 (5)0.0015 (4)0.0023 (4)0.0035 (4)
O50.0847 (10)0.0674 (9)0.0627 (8)0.0246 (8)0.0264 (7)0.0068 (7)
C30.0244 (5)0.0245 (5)0.0345 (6)0.0000 (4)0.0020 (4)0.0036 (5)
C70.0291 (6)0.0276 (6)0.0317 (6)0.0040 (5)0.0005 (5)0.0014 (5)
C20.0255 (5)0.0270 (6)0.0280 (6)0.0019 (4)0.0003 (4)0.0017 (4)
C60.0255 (5)0.0315 (6)0.0328 (6)0.0028 (5)0.0015 (4)0.0029 (5)
C80.0300 (6)0.0328 (6)0.0338 (6)0.0043 (5)0.0027 (5)0.0038 (5)
C40.0361 (6)0.0258 (6)0.0378 (7)0.0017 (5)0.0033 (5)0.0043 (5)
C100.0246 (6)0.0370 (7)0.0503 (8)0.0012 (5)0.0041 (5)0.0020 (6)
C10.0387 (7)0.0324 (6)0.0299 (6)0.0015 (5)0.0039 (5)0.0014 (5)
C50.0359 (6)0.0347 (7)0.0322 (6)0.0006 (5)0.0069 (5)0.0035 (5)
C140.0602 (9)0.0360 (7)0.0318 (7)0.0045 (6)0.0101 (6)0.0046 (5)
C90.0301 (6)0.0338 (7)0.0421 (7)0.0056 (5)0.0003 (5)0.0092 (5)
C130.0365 (8)0.0535 (10)0.0755 (12)0.0114 (7)0.0156 (8)0.0007 (8)
C120.0475 (9)0.0467 (9)0.0888 (14)0.0142 (7)0.0091 (9)0.0114 (9)
C110.0361 (8)0.0702 (11)0.0554 (10)0.0000 (8)0.0105 (7)0.0037 (8)
C150.0484 (14)0.0491 (12)0.0446 (13)0.0059 (11)0.0156 (10)0.0001 (9)
C160.086 (2)0.0770 (18)0.0488 (14)0.0114 (15)0.0205 (13)0.0207 (14)
C15A0.067 (8)0.059 (6)0.034 (5)0.020 (5)0.023 (5)0.015 (4)
C16A0.078 (9)0.075 (8)0.055 (7)0.019 (7)0.009 (6)0.019 (6)
Geometric parameters (Å, º) top
O1—H10.8200C10—C111.518 (2)
O1—C11.4183 (16)C1—H1C0.9700
O2—H20.8200C1—H1D0.9700
O2—C31.3656 (14)C5—H50.9300
O3—H30.8200C14—C151.504 (3)
O3—C81.4130 (16)C14—C15A1.580 (10)
O4—C141.2602 (19)C9—H9A0.9700
N1—H1A0.8900C9—H9B0.9700
N1—H1B0.8900C13—H13A0.9600
N1—C101.5208 (16)C13—H13B0.9600
N1—C91.4950 (16)C13—H13C0.9600
O5—C141.238 (2)C12—H12A0.9600
C3—C21.3979 (17)C12—H12B0.9600
C3—C41.3858 (18)C12—H12C0.9600
C7—H70.9300C11—H11A0.9600
C7—C21.3895 (17)C11—H11B0.9600
C7—C61.3914 (18)C11—H11C0.9600
C2—C11.5108 (17)C15—H150.9300
C6—C81.5179 (17)C15—C161.288 (4)
C6—C51.3908 (18)C16—H16A0.9300
C8—H80.9800C16—H16B0.9300
C8—C91.5193 (18)C15A—H15A0.9300
C4—H40.9300C15A—C16A1.279 (14)
C4—C51.3876 (19)C16A—H16C0.9300
C10—C131.526 (2)C16A—H16D0.9300
C10—C121.515 (2)
C1—O1—H1109.5C4—C5—C6120.62 (12)
C3—O2—H2109.5C4—C5—H5119.7
C8—O3—H3109.5O4—C14—C15122.80 (17)
H1A—N1—H1B107.2O4—C14—C15A97.9 (4)
C10—N1—H1A108.0O5—C14—O4122.95 (14)
C10—N1—H1B108.0O5—C14—C15114.02 (17)
C9—N1—H1A108.0O5—C14—C15A137.5 (4)
C9—N1—H1B108.0N1—C9—C8111.61 (11)
C9—N1—C10117.27 (10)N1—C9—H9A109.3
O2—C3—C2117.08 (11)N1—C9—H9B109.3
O2—C3—C4122.65 (11)C8—C9—H9A109.3
C4—C3—C2120.27 (11)C8—C9—H9B109.3
C2—C7—H7119.0H9A—C9—H9B108.0
C2—C7—C6121.92 (11)C10—C13—H13A109.5
C6—C7—H7119.0C10—C13—H13B109.5
C3—C2—C1118.80 (11)C10—C13—H13C109.5
C7—C2—C3118.53 (11)H13A—C13—H13B109.5
C7—C2—C1122.66 (11)H13A—C13—H13C109.5
C7—C6—C8119.78 (11)H13B—C13—H13C109.5
C5—C6—C7118.42 (11)C10—C12—H12A109.5
C5—C6—C8121.79 (11)C10—C12—H12B109.5
O3—C8—C6109.18 (10)C10—C12—H12C109.5
O3—C8—H8108.8H12A—C12—H12B109.5
O3—C8—C9111.64 (11)H12A—C12—H12C109.5
C6—C8—H8108.8H12B—C12—H12C109.5
C6—C8—C9109.56 (11)C10—C11—H11A109.5
C9—C8—H8108.8C10—C11—H11B109.5
C3—C4—H4119.9C10—C11—H11C109.5
C3—C4—C5120.19 (12)H11A—C11—H11B109.5
C5—C4—H4119.9H11A—C11—H11C109.5
N1—C10—C13105.57 (12)H11B—C11—H11C109.5
C12—C10—N1109.07 (12)C14—C15—H15118.5
C12—C10—C13110.33 (14)C16—C15—C14122.9 (3)
C12—C10—C11112.05 (15)C16—C15—H15118.5
C11—C10—N1109.59 (11)C15—C16—H16A120.0
C11—C10—C13110.03 (14)C15—C16—H16B120.0
O1—C1—C2113.46 (11)H16A—C16—H16B120.0
O1—C1—H1C108.9C14—C15A—H15A121.7
O1—C1—H1D108.9C16A—C15A—C14116.6 (12)
C2—C1—H1C108.9C16A—C15A—H15A121.7
C2—C1—H1D108.9C15A—C16A—H16C120.0
H1C—C1—H1D107.7C15A—C16A—H16D120.0
C6—C5—H5119.7H16C—C16A—H16D120.0
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
O1—H1···O3i0.821.982.7817 (14)166
O2—H2···O1ii0.821.962.7816 (14)174
O3—H3···O40.821.902.7194 (15)179
N1—H1A···O4iii0.891.922.8022 (16)171
N1—H1B···O50.891.962.8292 (18)166
Symmetry codes: (i) x, y+1/2, z+1/2; (ii) x, y1/2, z+3/2; (iii) x+1, y+1, z+1.
 

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