Buy article online - an online subscription or single-article purchase is required to access this article.
Download citation
Download citation
link to html
The title Schiff base compound, C12H17NO3, synthesized by the reaction of paeonol and isopropanolamine in absolute methanol, crystallizes in a zwitterionic form. All non-H atoms, except for the 2-hydroxy­propyl group, are approximately coplanar. The mol­ecules are linked to each other by intermolecular hydrogen bonds.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536806050276/ww2054sup1.cif
Contains datablocks I, global

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S1600536806050276/ww2054Isup2.hkl
Contains datablock I

CCDC reference: 632398

Key indicators

  • Single-crystal X-ray study
  • T = 296 K
  • Mean [sigma](C-C) = 0.003 Å
  • R factor = 0.041
  • wR factor = 0.081
  • Data-to-parameter ratio = 14.1

checkCIF/PLATON results

No syntax errors found



Alert level C CELLV02_ALERT_1_C The supplied cell volume s.u. differs from that calculated from the cell parameter s.u.'s by > 2 Calculated cell volume su = 36.12 Cell volume su given = 34.00 PLAT026_ALERT_3_C Ratio Observed / Unique Reflections too Low .... 49 Perc. PLAT152_ALERT_1_C Supplied and Calc Volume s.u. Inconsistent ..... ? PLAT230_ALERT_2_C Hirshfeld Test Diff for C5 - C6 .. 5.32 su PLAT720_ALERT_4_C Number of Unusual/Non-Standard Label(s) ........ 1
0 ALERT level A = In general: serious problem 0 ALERT level B = Potentially serious problem 5 ALERT level C = Check and explain 0 ALERT level G = General alerts; check 2 ALERT type 1 CIF construction/syntax error, inconsistent or missing data 1 ALERT type 2 Indicator that the structure model may be wrong or deficient 1 ALERT type 3 Indicator that the structure quality may be low 1 ALERT type 4 Improvement, methodology, query or suggestion 0 ALERT type 5 Informative message, check

Computing details top

Data collection: XSCANS (Siemens, 1994); cell refinement: XSCANS; data reduction: SHELXTL (Siemens, 1995); program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: SHELXTL; software used to prepare material for publication: SHELXTL.

2-[1-(2-Hydroxypropyliminio)ethyl]-5-methoxyphenolate top
Crystal data top
C12H17NO3Z = 2
Mr = 223.27F(000) = 240
Triclinic, P1Dx = 1.259 Mg m3
Hall symbol: -P 1Mo Kα radiation, λ = 0.71073 Å
a = 5.714 (2) ÅCell parameters from 35 reflections
b = 9.672 (4) Åθ = 3.1–12.4°
c = 10.869 (3) ŵ = 0.09 mm1
α = 98.19 (2)°T = 296 K
β = 96.71 (2)°Block, yellow
γ = 93.35 (3)°0.54 × 0.46 × 0.12 mm
V = 588.8 (3) Å3
Data collection top
Siemens P4
diffractometer
Rint = 0.017
Radiation source: normal-focus sealed tubeθmax = 25.5°, θmin = 1.9°
Graphite monochromatorh = 06
ω scansk = 1111
2506 measured reflectionsl = 1313
2187 independent reflections3 standard reflections every 97 reflections
1070 reflections with I > 2σ(I) intensity decay: 3.9%
Refinement top
Refinement on F2Secondary atom site location: difference Fourier map
Least-squares matrix: fullHydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.041H atoms treated by a mixture of independent and constrained refinement
wR(F2) = 0.081 w = 1/[σ2(Fo2) + (0.0268P)2]
where P = (Fo2 + 2Fc2)/3
S = 0.99(Δ/σ)max < 0.001
2187 reflectionsΔρmax = 0.15 e Å3
155 parametersΔρmin = 0.15 e Å3
2 restraintsExtinction correction: SHELXL97, Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4
Primary atom site location: structure-invariant direct methodsExtinction coefficient: 0.013 (2)
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*/UeqOcc. (<1)
O10.1251 (2)0.16218 (15)0.37940 (13)0.0595 (4)
O20.2213 (3)0.37187 (15)0.01565 (13)0.0661 (5)
O30.1269 (3)0.08674 (17)0.69327 (15)0.0600 (4)
N0.4475 (3)0.21279 (18)0.56303 (15)0.0474 (5)
C10.2480 (4)0.2422 (2)0.32170 (18)0.0446 (5)
C20.1621 (4)0.2657 (2)0.19827 (18)0.0495 (6)
H20.01500.22460.16090.059*
C30.2899 (4)0.3465 (2)0.13438 (19)0.0486 (6)
C40.5101 (4)0.4122 (2)0.18852 (19)0.0526 (6)
H40.59660.46810.14430.063*
C50.5961 (4)0.3935 (2)0.30633 (19)0.0506 (6)
H50.74260.43750.34130.061*
C60.4737 (3)0.31045 (19)0.37786 (18)0.0403 (5)
C70.5699 (3)0.2916 (2)0.50153 (18)0.0415 (5)
C80.8039 (3)0.3596 (2)0.56320 (18)0.0543 (6)
H8A0.83560.33430.64540.065*0.50
H8B0.80100.45950.56970.065*0.50
H8C0.92540.32880.51410.065*0.50
H8D0.87240.41410.50740.065*0.50
H8E0.90700.28890.58310.065*0.50
H8F0.78260.41960.63880.065*0.50
C90.5161 (4)0.1842 (2)0.69031 (18)0.0523 (6)
H9A0.49390.26510.75040.063*
H9B0.68190.16610.70090.063*
C100.3682 (4)0.0592 (2)0.71358 (19)0.0527 (6)
H100.39560.02230.65380.063*
C110.4376 (4)0.0290 (2)0.84557 (19)0.0698 (7)
H11A0.41230.10860.90480.084*
H11B0.60140.01060.85600.084*
H11C0.34290.05130.85940.084*
C120.0019 (4)0.3077 (3)0.0468 (2)0.0782 (8)
H12A0.00030.20770.05420.094*
H12B0.02900.33420.12890.094*
H12C0.12570.33840.00070.094*
H3O0.052 (5)0.0089 (17)0.672 (3)0.142 (14)*
H0N0.315 (3)0.176 (3)0.520 (3)0.170*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
O10.0500 (10)0.0712 (10)0.0547 (10)0.0145 (8)0.0006 (8)0.0148 (8)
O20.0760 (12)0.0763 (11)0.0453 (9)0.0046 (9)0.0014 (9)0.0149 (8)
O30.0487 (10)0.0584 (11)0.0724 (11)0.0011 (9)0.0045 (8)0.0124 (9)
N0.0436 (12)0.0533 (12)0.0437 (11)0.0019 (10)0.0001 (9)0.0088 (9)
C10.0421 (14)0.0441 (13)0.0459 (14)0.0013 (11)0.0061 (11)0.0013 (11)
C20.0439 (14)0.0549 (14)0.0471 (13)0.0007 (11)0.0004 (11)0.0048 (11)
C30.0534 (15)0.0515 (14)0.0409 (13)0.0096 (12)0.0047 (11)0.0053 (11)
C40.0518 (15)0.0564 (15)0.0515 (14)0.0016 (12)0.0110 (12)0.0128 (11)
C50.0417 (13)0.0548 (14)0.0536 (14)0.0025 (11)0.0052 (11)0.0061 (11)
C60.0377 (13)0.0378 (12)0.0438 (12)0.0020 (10)0.0057 (10)0.0025 (10)
C70.0367 (12)0.0394 (12)0.0471 (13)0.0010 (10)0.0060 (11)0.0021 (10)
C80.0425 (13)0.0637 (15)0.0550 (14)0.0051 (11)0.0014 (11)0.0105 (11)
C90.0493 (14)0.0592 (15)0.0468 (14)0.0030 (12)0.0012 (11)0.0111 (11)
C100.0528 (15)0.0505 (14)0.0528 (14)0.0037 (12)0.0013 (11)0.0062 (11)
C110.0779 (18)0.0716 (17)0.0617 (16)0.0029 (14)0.0015 (13)0.0231 (13)
C120.0779 (19)0.100 (2)0.0516 (15)0.0149 (16)0.0089 (14)0.0053 (14)
Geometric parameters (Å, º) top
O1—C11.290 (2)C7—C81.494 (2)
O2—C31.365 (2)C8—H8A0.9600
O2—C121.434 (2)C8—H8B0.9600
O3—C101.417 (2)C8—H8C0.9600
O3—H3O0.833 (10)C8—H8D0.9600
N—C71.307 (2)C8—H8E0.9600
N—C91.463 (2)C8—H8F0.9600
N—H0N0.869 (10)C9—C101.503 (3)
C1—C21.428 (2)C9—H9A0.9700
C1—C61.440 (2)C9—H9B0.9700
C2—C31.354 (3)C10—C111.517 (3)
C2—H20.9300C10—H100.9800
C3—C41.400 (3)C11—H11A0.9600
C4—C51.358 (2)C11—H11B0.9600
C4—H40.9300C11—H11C0.9600
C5—C61.406 (3)C12—H12A0.9600
C5—H50.9300C12—H12B0.9600
C6—C71.432 (2)C12—H12C0.9600
C3—O2—C12117.86 (17)C7—C8—H8E109.5
C10—O3—H3O106 (2)H8A—C8—H8E56.3
C7—N—C9126.09 (17)H8B—C8—H8E141.1
C7—N—H0N113 (2)H8C—C8—H8E56.3
C9—N—H0N121 (2)H8D—C8—H8E109.5
O1—C1—C2120.25 (19)C7—C8—H8F109.5
O1—C1—C6122.02 (19)H8A—C8—H8F56.3
C2—C1—C6117.73 (19)H8B—C8—H8F56.3
C3—C2—C1121.5 (2)H8C—C8—H8F141.1
C3—C2—H2119.2H8D—C8—H8F109.5
C1—C2—H2119.2H8E—C8—H8F109.5
C2—C3—O2124.8 (2)N—C9—C10109.68 (16)
C2—C3—C4120.8 (2)N—C9—H9A109.7
O2—C3—C4114.3 (2)C10—C9—H9A109.7
C5—C4—C3119.2 (2)N—C9—H9B109.7
C5—C4—H4120.4C10—C9—H9B109.7
C3—C4—H4120.4H9A—C9—H9B108.2
C4—C5—C6123.0 (2)O3—C10—C9108.45 (18)
C4—C5—H5118.5O3—C10—C11111.66 (18)
C6—C5—H5118.5C9—C10—C11110.06 (17)
C5—C6—C7121.74 (19)O3—C10—H10108.9
C5—C6—C1117.67 (19)C9—C10—H10108.9
C7—C6—C1120.59 (18)C11—C10—H10108.9
N—C7—C6118.74 (18)C10—C11—H11A109.5
N—C7—C8118.83 (18)C10—C11—H11B109.5
C6—C7—C8122.44 (18)H11A—C11—H11B109.5
C7—C8—H8A109.5C10—C11—H11C109.5
C7—C8—H8B109.5H11A—C11—H11C109.5
H8A—C8—H8B109.5H11B—C11—H11C109.5
C7—C8—H8C109.5O2—C12—H12A109.5
H8A—C8—H8C109.5O2—C12—H12B109.5
H8B—C8—H8C109.5H12A—C12—H12B109.5
C7—C8—H8D109.5O2—C12—H12C109.5
H8A—C8—H8D141.1H12A—C12—H12C109.5
H8B—C8—H8D56.3H12B—C12—H12C109.5
H8C—C8—H8D56.3
O1—C1—C2—C3178.43 (19)C2—C1—C6—C51.2 (3)
C6—C1—C2—C31.6 (3)O1—C1—C6—C70.2 (3)
C1—C2—C3—O2178.90 (18)C2—C1—C6—C7179.85 (19)
C1—C2—C3—C41.2 (3)C9—N—C7—C6178.84 (18)
C12—O2—C3—C20.4 (3)C9—N—C7—C80.7 (3)
C12—O2—C3—C4179.66 (18)C5—C6—C7—N179.82 (19)
C2—C3—C4—C50.4 (3)C1—C6—C7—N0.9 (3)
O2—C3—C4—C5179.66 (19)C5—C6—C7—C80.7 (3)
C3—C4—C5—C60.1 (3)C1—C6—C7—C8179.64 (18)
C4—C5—C6—C7179.4 (2)C7—N—C9—C10163.7 (2)
C4—C5—C6—C10.5 (3)N—C9—C10—O357.4 (2)
O1—C1—C6—C5178.81 (19)N—C9—C10—C11179.81 (18)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
O3—H3O···O1i0.83 (1)1.87 (2)2.698 (2)178 (3)
N—H0N···O10.87 (1)1.75 (2)2.525 (2)147 (3)
Symmetry code: (i) x, y, z+1.
 

Subscribe to Acta Crystallographica Section E: Crystallographic Communications

The full text of this article is available to subscribers to the journal.

If you have already registered and are using a computer listed in your registration details, please email support@iucr.org for assistance.

Buy online

You may purchase this article in PDF and/or HTML formats. For purchasers in the European Community who do not have a VAT number, VAT will be added at the local rate. Payments to the IUCr are handled by WorldPay, who will accept payment by credit card in several currencies. To purchase the article, please complete the form below (fields marked * are required), and then click on `Continue'.
E-mail address* 
Repeat e-mail address* 
(for error checking) 

Format*   PDF (US $40)
   HTML (US $40)
   PDF+HTML (US $50)
In order for VAT to be shown for your country javascript needs to be enabled.

VAT number 
(non-UK EC countries only) 
Country* 
 

Terms and conditions of use
Contact us

Follow Acta Cryst. E
Sign up for e-alerts
Follow Acta Cryst. on Twitter
Follow us on facebook
Sign up for RSS feeds