2-[1-(2-Hydroxy­propyl­iminio)eth­yl]-5-methoxy­phenolate

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.

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

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Computing details

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

Crystal data

C12H17NO3	Z = 2
Mr = 223.27	F(000) = 240
Triclinic, P1	Dx = 1.259 Mg m^−3
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 5.714 (2) Å	Cell parameters from 35 reflections
b = 9.672 (4) Å	θ = 3.1–12.4°
c = 10.869 (3) Å	µ = 0.09 mm^−1
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) Å^3

Data collection

Siemens P4 diffractometer	Rint = 0.017
Radiation source: normal-focus sealed tube	θmax = 25.5°, θmin = 1.9°
Graphite monochromator	h = 0→6
ω scans	k = −11→11
2506 measured reflections	l = −13→13
2187 independent reflections	3 standard reflections every 97 reflections
1070 reflections with I > 2σ(I)	intensity decay: 3.9%

Refinement

Refinement on F^2	Secondary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F^2 > 2σ(F^2)] = 0.041	H atoms treated by a mixture of independent and constrained refinement
wR(F^2) = 0.081	w = 1/[σ^2(Fo^2) + (0.0268P)^2] where P = (Fo^2 + 2Fc^2)/3
S = 0.99	(Δ/σ)max < 0.001
2187 reflections	Δρmax = 0.15 e Å^−3
155 parameters	Δρmin = −0.15 e Å^−3
2 restraints	Extinction correction: SHELXL97, Fc^*=kFc[1+0.001xFc^2λ^3/sin(2θ)]^-1/4
Primary atom site location: structure-invariant direct methods	Extinction coefficient: 0.013 (2)

Special details

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 (Ų)

	x	y	z	Uiso*/Ueq	Occ. (<1)
O1	0.1251 (2)	0.16218 (15)	0.37940 (13)	0.0595 (4)
O2	0.2213 (3)	0.37187 (15)	0.01565 (13)	0.0661 (5)
O3	0.1269 (3)	0.08674 (17)	0.69327 (15)	0.0600 (4)
N	0.4475 (3)	0.21279 (18)	0.56303 (15)	0.0474 (5)
C1	0.2480 (4)	0.2422 (2)	0.32170 (18)	0.0446 (5)
C2	0.1621 (4)	0.2657 (2)	0.19827 (18)	0.0495 (6)
H2	0.0150	0.2246	0.1609	0.059*
C3	0.2899 (4)	0.3465 (2)	0.13438 (19)	0.0486 (6)
C4	0.5101 (4)	0.4122 (2)	0.18852 (19)	0.0526 (6)
H4	0.5966	0.4681	0.1443	0.063*
C5	0.5961 (4)	0.3935 (2)	0.30633 (19)	0.0506 (6)
H5	0.7426	0.4375	0.3413	0.061*
C6	0.4737 (3)	0.31045 (19)	0.37786 (18)	0.0403 (5)
C7	0.5699 (3)	0.2916 (2)	0.50153 (18)	0.0415 (5)
C8	0.8039 (3)	0.3596 (2)	0.56320 (18)	0.0543 (6)
H8A	0.8356	0.3343	0.6454	0.065*	0.50
H8B	0.8010	0.4595	0.5697	0.065*	0.50
H8C	0.9254	0.3288	0.5141	0.065*	0.50
H8D	0.8724	0.4141	0.5074	0.065*	0.50
H8E	0.9070	0.2889	0.5831	0.065*	0.50
H8F	0.7826	0.4196	0.6388	0.065*	0.50
C9	0.5161 (4)	0.1842 (2)	0.69031 (18)	0.0523 (6)
H9A	0.4939	0.2651	0.7504	0.063*
H9B	0.6819	0.1661	0.7009	0.063*
C10	0.3682 (4)	0.0592 (2)	0.71358 (19)	0.0527 (6)
H10	0.3956	−0.0223	0.6538	0.063*
C11	0.4376 (4)	0.0290 (2)	0.84557 (19)	0.0698 (7)
H11A	0.4123	0.1086	0.9048	0.084*
H11B	0.6014	0.0106	0.8560	0.084*
H11C	0.3429	−0.0513	0.8594	0.084*
C12	−0.0019 (4)	0.3077 (3)	−0.0468 (2)	0.0782 (8)
H12A	−0.0003	0.2077	−0.0542	0.094*
H12B	−0.0290	0.3342	−0.1289	0.094*
H12C	−0.1257	0.3384	0.0007	0.094*
H3O	0.052 (5)	0.0089 (17)	0.672 (3)	0.142 (14)*
H0N	0.315 (3)	0.176 (3)	0.520 (3)	0.170*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
O1	0.0500 (10)	0.0712 (10)	0.0547 (10)	−0.0145 (8)	−0.0006 (8)	0.0148 (8)
O2	0.0760 (12)	0.0763 (11)	0.0453 (9)	0.0046 (9)	−0.0014 (9)	0.0149 (8)
O3	0.0487 (10)	0.0584 (11)	0.0724 (11)	0.0011 (9)	0.0045 (8)	0.0124 (9)
N	0.0436 (12)	0.0533 (12)	0.0437 (11)	−0.0019 (10)	−0.0001 (9)	0.0088 (9)
C1	0.0421 (14)	0.0441 (13)	0.0459 (14)	0.0013 (11)	0.0061 (11)	0.0013 (11)
C2	0.0439 (14)	0.0549 (14)	0.0471 (13)	0.0007 (11)	−0.0004 (11)	0.0048 (11)
C3	0.0534 (15)	0.0515 (14)	0.0409 (13)	0.0096 (12)	0.0047 (11)	0.0053 (11)
C4	0.0518 (15)	0.0564 (15)	0.0515 (14)	−0.0016 (12)	0.0110 (12)	0.0128 (11)
C5	0.0417 (13)	0.0548 (14)	0.0536 (14)	−0.0025 (11)	0.0052 (11)	0.0061 (11)
C6	0.0377 (13)	0.0378 (12)	0.0438 (12)	−0.0020 (10)	0.0057 (10)	0.0025 (10)
C7	0.0367 (12)	0.0394 (12)	0.0471 (13)	0.0010 (10)	0.0060 (11)	0.0021 (10)
C8	0.0425 (13)	0.0637 (15)	0.0550 (14)	−0.0051 (11)	0.0014 (11)	0.0105 (11)
C9	0.0493 (14)	0.0592 (15)	0.0468 (14)	−0.0030 (12)	−0.0012 (11)	0.0111 (11)
C10	0.0528 (15)	0.0505 (14)	0.0528 (14)	0.0037 (12)	0.0013 (11)	0.0062 (11)
C11	0.0779 (18)	0.0716 (17)	0.0617 (16)	0.0029 (14)	0.0015 (13)	0.0231 (13)
C12	0.0779 (19)	0.100 (2)	0.0516 (15)	0.0149 (16)	−0.0089 (14)	0.0053 (14)

Geometric parameters (Å, º)

O1—C1	1.290 (2)	C7—C8	1.494 (2)
O2—C3	1.365 (2)	C8—H8A	0.9600
O2—C12	1.434 (2)	C8—H8B	0.9600
O3—C10	1.417 (2)	C8—H8C	0.9600
O3—H3O	0.833 (10)	C8—H8D	0.9600
N—C7	1.307 (2)	C8—H8E	0.9600
N—C9	1.463 (2)	C8—H8F	0.9600
N—H0N	0.869 (10)	C9—C10	1.503 (3)
C1—C2	1.428 (2)	C9—H9A	0.9700
C1—C6	1.440 (2)	C9—H9B	0.9700
C2—C3	1.354 (3)	C10—C11	1.517 (3)
C2—H2	0.9300	C10—H10	0.9800
C3—C4	1.400 (3)	C11—H11A	0.9600
C4—C5	1.358 (2)	C11—H11B	0.9600
C4—H4	0.9300	C11—H11C	0.9600
C5—C6	1.406 (3)	C12—H12A	0.9600
C5—H5	0.9300	C12—H12B	0.9600
C6—C7	1.432 (2)	C12—H12C	0.9600
C3—O2—C12	117.86 (17)	C7—C8—H8E	109.5
C10—O3—H3O	106 (2)	H8A—C8—H8E	56.3
C7—N—C9	126.09 (17)	H8B—C8—H8E	141.1
C7—N—H0N	113 (2)	H8C—C8—H8E	56.3
C9—N—H0N	121 (2)	H8D—C8—H8E	109.5
O1—C1—C2	120.25 (19)	C7—C8—H8F	109.5
O1—C1—C6	122.02 (19)	H8A—C8—H8F	56.3
C2—C1—C6	117.73 (19)	H8B—C8—H8F	56.3
C3—C2—C1	121.5 (2)	H8C—C8—H8F	141.1
C3—C2—H2	119.2	H8D—C8—H8F	109.5
C1—C2—H2	119.2	H8E—C8—H8F	109.5
C2—C3—O2	124.8 (2)	N—C9—C10	109.68 (16)
C2—C3—C4	120.8 (2)	N—C9—H9A	109.7
O2—C3—C4	114.3 (2)	C10—C9—H9A	109.7
C5—C4—C3	119.2 (2)	N—C9—H9B	109.7
C5—C4—H4	120.4	C10—C9—H9B	109.7
C3—C4—H4	120.4	H9A—C9—H9B	108.2
C4—C5—C6	123.0 (2)	O3—C10—C9	108.45 (18)
C4—C5—H5	118.5	O3—C10—C11	111.66 (18)
C6—C5—H5	118.5	C9—C10—C11	110.06 (17)
C5—C6—C7	121.74 (19)	O3—C10—H10	108.9
C5—C6—C1	117.67 (19)	C9—C10—H10	108.9
C7—C6—C1	120.59 (18)	C11—C10—H10	108.9
N—C7—C6	118.74 (18)	C10—C11—H11A	109.5
N—C7—C8	118.83 (18)	C10—C11—H11B	109.5
C6—C7—C8	122.44 (18)	H11A—C11—H11B	109.5
C7—C8—H8A	109.5	C10—C11—H11C	109.5
C7—C8—H8B	109.5	H11A—C11—H11C	109.5
H8A—C8—H8B	109.5	H11B—C11—H11C	109.5
C7—C8—H8C	109.5	O2—C12—H12A	109.5
H8A—C8—H8C	109.5	O2—C12—H12B	109.5
H8B—C8—H8C	109.5	H12A—C12—H12B	109.5
C7—C8—H8D	109.5	O2—C12—H12C	109.5
H8A—C8—H8D	141.1	H12A—C12—H12C	109.5
H8B—C8—H8D	56.3	H12B—C12—H12C	109.5
H8C—C8—H8D	56.3
O1—C1—C2—C3	−178.43 (19)	C2—C1—C6—C5	−1.2 (3)
C6—C1—C2—C3	1.6 (3)	O1—C1—C6—C7	−0.2 (3)
C1—C2—C3—O2	178.90 (18)	C2—C1—C6—C7	179.85 (19)
C1—C2—C3—C4	−1.2 (3)	C9—N—C7—C6	−178.84 (18)
C12—O2—C3—C2	−0.4 (3)	C9—N—C7—C8	0.7 (3)
C12—O2—C3—C4	179.66 (18)	C5—C6—C7—N	−179.82 (19)
C2—C3—C4—C5	0.4 (3)	C1—C6—C7—N	−0.9 (3)
O2—C3—C4—C5	−179.66 (19)	C5—C6—C7—C8	0.7 (3)
C3—C4—C5—C6	−0.1 (3)	C1—C6—C7—C8	179.64 (18)
C4—C5—C6—C7	179.4 (2)	C7—N—C9—C10	−163.7 (2)
C4—C5—C6—C1	0.5 (3)	N—C9—C10—O3	−57.4 (2)
O1—C1—C6—C5	178.81 (19)	N—C9—C10—C11	−179.81 (18)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
O3—H3O···O1^i	0.83 (1)	1.87 (2)	2.698 (2)	178 (3)
N—H0N···O1	0.87 (1)	1.75 (2)	2.525 (2)	147 (3)

Symmetry code: (i) −x, −y, −z+1.