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In the crystal of the title compound, C17H30NO2+·C2HO4, the centrosymmetrically related cations form dimeric pairs through N—H...O hydrogen bonds. The anions are linked by O—H...O hydrogen bonds to form infinite one-dimensional chains along the b axis. The anions and the cations are linked by intermolecular N—H...O and O—H...O hydrogen bonds to form a molecular network.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536802000089/ci6089sup1.cif
Contains datablocks I, global

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S1600536802000089/ci6089Isup2.hkl
Contains datablock I

CCDC reference: 180770

Key indicators

  • Single-crystal X-ray study
  • T = 293 K
  • Mean [sigma](C-C) = 0.003 Å
  • R factor = 0.050
  • wR factor = 0.157
  • Data-to-parameter ratio = 15.7

checkCIF results

No syntax errors found

ADDSYM reports no extra symmetry


Yellow Alert Alert Level C:
PLAT_369 Alert C Long C(sp2)-C(sp2) Bond C(21) - C(24) = 1.53 Ang.
0 Alert Level A = Potentially serious problem
0 Alert Level B = Potential problem
1 Alert Level C = Please check

Computing details top

Data collection: CAD-4 EXPRESS (Enraf-Nonius, 1994); cell refinement: CAD-4 EXPRESS; data reduction: MolEN (Fair, 1990); program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: ZORTEP (Zsolnai, 1997); software used to prepare material for publication: SHELXL97.

N-(3-(2-isopropyl-5-methylphenoxy)-2-hydroxypropyl-N-(tert-butyl)ammonium oxalate top
Crystal data top
C17H30NO2+·C2HO4F(000) = 800
Mr = 369.45Dx = 1.196 Mg m3
Monoclinic, P21/nCu Kα radiation, λ = 1.5418 Å
a = 12.908 (2) ÅCell parameters from 25 reflections
b = 10.763 (1) Åθ = 20–30°
c = 15.784 (2) ŵ = 0.73 mm1
β = 110.648 (11)°T = 293 K
V = 2052.0 (5) Å3Plate, white
Z = 40.30 × 0.15 × 0.10 mm
Data collection top
Enraf-Nonius CAD-4
diffractometer
3066 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tubeRint = 0.030
Graphite monochromatorθmax = 67.9°, θmin = 3.8°
ω–2θ scansh = 1514
Absorption correction: ψ scan
(North et al., 1968)
k = 012
Tmin = 0.812, Tmax = 0.931l = 1718
4071 measured reflections2 standard reflections every 120 min
3723 independent reflections intensity decay: none
Refinement top
Refinement on F2Primary atom site location: structure-invariant direct methods
Least-squares matrix: fullSecondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.050Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.157H-atom parameters constrained
S = 1.06 w = 1/[σ2(Fo2) + (0.0912P)2 + 0.5356P]
where P = (Fo2 + 2Fc2)/3
3723 reflections(Δ/σ)max = 0.001
237 parametersΔρmax = 0.58 e Å3
0 restraintsΔρmin = 0.25 e Å3
Special details top

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.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/Ueq
C10.70874 (14)0.64384 (17)0.32720 (11)0.0415 (4)
C20.65364 (16)0.57151 (19)0.25048 (12)0.0495 (4)
C30.7191 (2)0.4926 (2)0.22250 (15)0.0660 (6)
H30.68550.44160.17280.079*
C40.8332 (2)0.4859 (2)0.26537 (16)0.0682 (6)
H40.87400.43090.24410.082*
C50.88639 (17)0.5597 (2)0.33910 (14)0.0542 (5)
C60.82258 (15)0.63873 (18)0.37021 (12)0.0470 (4)
H60.85660.68870.42040.056*
O70.64151 (10)0.71887 (13)0.35561 (8)0.0517 (4)
C80.68755 (14)0.78336 (16)0.43933 (11)0.0420 (4)
H8A0.73960.84630.43560.050*
H8B0.72540.72630.48800.050*
C90.58878 (14)0.84247 (15)0.45476 (11)0.0393 (4)
H90.54160.87940.39740.047*
C100.52172 (13)0.74446 (15)0.48079 (11)0.0380 (4)
H10A0.50850.67530.43890.046*
H10B0.56350.71370.54090.046*
N110.41386 (11)0.79460 (12)0.47964 (9)0.0373 (3)
H11A0.42120.87720.48860.045*
H11B0.36340.78240.42400.045*
C120.36815 (15)0.74063 (17)0.54817 (12)0.0455 (4)
C130.4420 (2)0.7841 (3)0.64180 (15)0.0744 (7)
H13A0.51450.74900.65620.112*
H13B0.41090.75770.68580.112*
H13C0.44710.87310.64240.112*
C140.25231 (19)0.7947 (3)0.5238 (2)0.0770 (7)
H14A0.25700.88350.52960.115*
H14B0.21790.76180.56390.115*
H14C0.20890.77300.46250.115*
C150.3645 (2)0.6007 (2)0.53975 (18)0.0724 (7)
H15A0.43850.56910.55570.109*
H15B0.32220.57780.47850.109*
H15C0.33050.56640.57970.109*
O160.62103 (11)0.93805 (11)0.51971 (8)0.0460 (3)
H160.66000.90910.56860.069*
C171.0116 (2)0.5582 (3)0.38387 (19)0.0804 (7)
H17A1.04230.49940.35350.121*
H17B1.03130.53500.44630.121*
H17C1.04040.63950.38010.121*
C180.52986 (18)0.5840 (2)0.20084 (14)0.0647 (6)
H180.49760.61340.24490.078*
C190.5059 (3)0.6806 (4)0.1280 (3)0.1241 (14)
H19A0.42730.68770.09770.186*
H19B0.53980.65690.08520.186*
H19C0.53540.75910.15460.186*
C200.4721 (3)0.4651 (3)0.1614 (3)0.1181 (13)
H20A0.48760.40340.20810.177*
H20B0.49810.43670.11480.177*
H20C0.39370.47930.13600.177*
C210.77785 (15)0.60106 (17)0.74565 (12)0.0482 (4)
O220.70216 (15)0.53935 (13)0.68431 (10)0.0721 (5)
H220.70810.46530.69730.108*
O230.85215 (17)0.55460 (14)0.80546 (13)0.0953 (7)
C240.76775 (15)0.74215 (17)0.73412 (12)0.0467 (4)
O250.79236 (14)0.80095 (12)0.80753 (9)0.0648 (4)
O260.74117 (14)0.78509 (13)0.65732 (9)0.0637 (4)
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
C10.0469 (9)0.0465 (9)0.0387 (8)0.0009 (7)0.0246 (7)0.0002 (7)
C20.0535 (10)0.0598 (11)0.0416 (9)0.0067 (9)0.0247 (8)0.0058 (8)
C30.0747 (14)0.0723 (14)0.0567 (11)0.0017 (11)0.0303 (10)0.0218 (10)
C40.0731 (14)0.0723 (14)0.0705 (14)0.0133 (12)0.0394 (11)0.0107 (11)
C50.0515 (11)0.0624 (12)0.0575 (11)0.0069 (9)0.0300 (9)0.0056 (9)
C60.0468 (10)0.0522 (10)0.0466 (9)0.0032 (8)0.0224 (8)0.0020 (8)
O70.0435 (7)0.0703 (9)0.0428 (7)0.0056 (6)0.0171 (5)0.0131 (6)
C80.0427 (9)0.0455 (9)0.0412 (9)0.0031 (7)0.0189 (7)0.0043 (7)
C90.0433 (9)0.0375 (8)0.0410 (8)0.0000 (7)0.0198 (7)0.0004 (7)
C100.0401 (9)0.0352 (8)0.0426 (9)0.0032 (7)0.0194 (7)0.0019 (6)
N110.0397 (7)0.0335 (7)0.0403 (7)0.0019 (6)0.0163 (6)0.0002 (5)
C120.0494 (10)0.0468 (10)0.0489 (10)0.0020 (8)0.0280 (8)0.0046 (8)
C130.0875 (17)0.0946 (18)0.0483 (12)0.0013 (14)0.0327 (11)0.0068 (11)
C140.0551 (13)0.0812 (16)0.108 (2)0.0007 (12)0.0449 (13)0.0147 (14)
C150.1012 (18)0.0487 (12)0.0839 (16)0.0110 (12)0.0533 (14)0.0125 (11)
O160.0537 (7)0.0382 (6)0.0436 (7)0.0029 (5)0.0141 (6)0.0013 (5)
C170.0545 (13)0.101 (2)0.0915 (17)0.0130 (13)0.0333 (12)0.0015 (15)
C180.0529 (11)0.0935 (17)0.0503 (11)0.0119 (11)0.0214 (9)0.0226 (11)
C190.0677 (18)0.110 (3)0.162 (3)0.0003 (18)0.000 (2)0.045 (3)
C200.091 (2)0.110 (2)0.125 (3)0.043 (2)0.0025 (19)0.010 (2)
C210.0536 (11)0.0395 (9)0.0423 (9)0.0006 (8)0.0055 (8)0.0006 (7)
O220.0844 (11)0.0421 (7)0.0607 (9)0.0065 (7)0.0103 (8)0.0017 (6)
O230.0957 (13)0.0426 (8)0.0944 (12)0.0002 (8)0.0325 (10)0.0086 (8)
C240.0487 (10)0.0404 (9)0.0418 (9)0.0016 (7)0.0044 (7)0.0021 (7)
O250.0940 (11)0.0405 (7)0.0430 (7)0.0118 (7)0.0031 (7)0.0015 (5)
O260.0825 (10)0.0512 (8)0.0475 (8)0.0060 (7)0.0107 (7)0.0085 (6)
Geometric parameters (Å, º) top
C1—O71.371 (2)C13—H13A0.96
C1—C61.386 (3)C13—H13B0.96
C1—C21.404 (2)C13—H13C0.96
C2—C31.376 (3)C14—H14A0.96
C2—C181.517 (3)C14—H14B0.96
C3—C41.388 (3)C14—H14C0.96
C3—H30.93C15—H15A0.96
C4—C51.376 (3)C15—H15B0.96
C4—H40.93C15—H15C0.96
C5—C61.389 (3)O16—H160.82
C5—C171.518 (3)C17—H17A0.96
C6—H60.93C17—H17B0.96
O7—C81.424 (2)C17—H17C0.96
C8—C91.519 (2)C18—C191.499 (4)
C8—H8A0.97C18—C201.501 (4)
C8—H8B0.97C18—H180.98
C9—O161.408 (2)C19—H19A0.96
C9—C101.511 (2)C19—H19B0.96
C9—H90.98C19—H19C0.96
C10—N111.487 (2)C20—H20A0.96
C10—H10A0.97C20—H20B0.96
C10—H10B0.97C20—H20C0.96
N11—C121.518 (2)C21—O231.193 (2)
N11—H11A0.90C21—O221.291 (2)
N11—H11B0.90C21—C241.529 (3)
C12—C151.511 (3)O22—H220.82
C12—C141.522 (3)C24—O261.228 (2)
C12—C131.523 (3)C24—O251.259 (2)
O7—C1—C6123.18 (15)C12—C13—H13B109.5
O7—C1—C2114.97 (15)H13A—C13—H13B109.5
C6—C1—C2121.85 (16)C12—C13—H13C109.5
C3—C2—C1115.94 (18)H13A—C13—H13C109.5
C3—C2—C18122.89 (18)H13B—C13—H13C109.5
C1—C2—C18121.14 (17)C12—C14—H14A109.5
C2—C3—C4122.8 (2)C12—C14—H14B109.5
C2—C3—H3118.6H14A—C14—H14B109.5
C4—C3—H3118.6C12—C14—H14C109.5
C5—C4—C3120.63 (19)H14A—C14—H14C109.5
C5—C4—H4119.7H14B—C14—H14C109.5
C3—C4—H4119.7C12—C15—H15A109.5
C4—C5—C6118.11 (19)C12—C15—H15B109.5
C4—C5—C17121.32 (19)H15A—C15—H15B109.5
C6—C5—C17120.5 (2)C12—C15—H15C109.5
C1—C6—C5120.65 (18)H15A—C15—H15C109.5
C1—C6—H6119.7H15B—C15—H15C109.5
C5—C6—H6119.7C9—O16—H16109.5
C1—O7—C8119.04 (13)C5—C17—H17A109.5
O7—C8—C9104.69 (13)C5—C17—H17B109.5
O7—C8—H8A110.8H17A—C17—H17B109.5
C9—C8—H8A110.8C5—C17—H17C109.5
O7—C8—H8B110.8H17A—C17—H17C109.5
C9—C8—H8B110.8H17B—C17—H17C109.5
H8A—C8—H8B108.9C19—C18—C20109.6 (2)
O16—C9—C10111.28 (13)C19—C18—C2110.6 (2)
O16—C9—C8111.92 (14)C20—C18—C2114.6 (2)
C10—C9—C8110.18 (14)C19—C18—H18107.2
O16—C9—H9107.8C20—C18—H18107.2
C10—C9—H9107.8C2—C18—H18107.2
C8—C9—H9107.8C18—C19—H19A109.5
N11—C10—C9111.53 (13)C18—C19—H19B109.5
N11—C10—H10A109.3H19A—C19—H19B109.5
C9—C10—H10A109.3C18—C19—H19C109.5
N11—C10—H10B109.3H19A—C19—H19C109.5
C9—C10—H10B109.3H19B—C19—H19C109.5
H10A—C10—H10B108.0C18—C20—H20A109.5
C10—N11—C12116.72 (13)C18—C20—H20B109.5
C10—N11—H11B108.1H20A—C20—H20B109.5
C12—N11—H11B108.1C18—C20—H20C109.5
C10—N11—H11A108.1H20A—C20—H20C109.5
C12—N11—H11A108.1H20B—C20—H20C109.5
H11B—N11—H11A107.3O23—C21—O22124.24 (18)
C15—C12—N11109.06 (15)O23—C21—C24121.43 (16)
C15—C12—C14111.20 (19)O22—C21—C24114.29 (15)
N11—C12—C14105.52 (15)C21—O22—H22109.5
C15—C12—C13112.40 (19)O26—C24—O25127.70 (17)
N11—C12—C13107.83 (16)O26—C24—C21118.27 (16)
C14—C12—C13110.52 (19)O25—C24—C21113.98 (15)
C12—C13—H13A109.5
O7—C1—C2—C3178.01 (18)O16—C9—C10—N1165.88 (17)
C6—C1—C2—C32.0 (3)C8—C9—C10—N11169.38 (13)
O7—C1—C2—C183.8 (3)C9—C10—N11—C12147.38 (14)
C6—C1—C2—C18176.23 (18)C10—N11—C12—C1553.1 (2)
C1—C2—C3—C41.5 (3)C10—N11—C12—C14172.60 (16)
C18—C2—C3—C4176.7 (2)C10—N11—C12—C1369.3 (2)
C2—C3—C4—C50.1 (4)C3—C2—C18—C1988.1 (3)
C3—C4—C5—C61.3 (3)C1—C2—C18—C1989.9 (3)
C3—C4—C5—C17176.9 (2)C3—C2—C18—C2036.4 (3)
O7—C1—C6—C5179.13 (17)C1—C2—C18—C20145.5 (2)
C2—C1—C6—C50.9 (3)O23—C21—C24—O26138.1 (2)
C4—C5—C6—C10.8 (3)O22—C21—C24—O2639.9 (3)
C17—C5—C6—C1177.4 (2)O23—C21—C24—O2539.5 (3)
C6—C1—O7—C88.1 (2)O22—C21—C24—O25142.5 (2)
C2—C1—O7—C8171.90 (15)C8—C9—O16—H1662.5
C1—O7—C8—C9172.97 (14)C10—C9—O16—H1661.3
O7—C8—C9—O16162.74 (13)C24—C21—O22—H22173.9
O7—C8—C9—C1072.89 (17)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
N11—H11A···O16i0.902.052.913 (2)159
N11—H11B···O25ii0.901.962.809 (2)157
N11—H11B···O23ii0.902.533.047 (2)117
O16—H16···O260.821.952.731 (2)159
O22—H22···O25iii0.821.772.569 (2)164
C9—H9···O23ii0.982.473.322 (3)146
C10—H10B···O260.972.503.227 (2)132
Symmetry codes: (i) x+1, y+2, z+1; (ii) x1/2, y+3/2, z1/2; (iii) x+3/2, y1/2, z+3/2.
 

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