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

The title Schiff base compound, C₁₁H₁₅NO₃, synthesized by the reaction of paeonol and ethano­lamine in absolute methanol, crystallizes in a zwitterionic form. All non-H atoms except the hydroxyl O atom are approximately coplanar. Mol­ecules are linked by O—H...O hydrogen bonds into chains along the [100] direction.

Key indicators

• Single-crystal X-ray study
• T = 293 K
• Mean [sigma](C-C) = 0.003 Å
• R factor = 0.037
• wR factor = 0.125
• Data-to-parameter ratio = 8.3

checkCIF/PLATON results

No syntax errors found



Alert level C
PLAT066_ALERT_1_C Predicted and Reported Transmissions Identical .          ?
PLAT380_ALERT_4_C Check Incorrectly? Oriented X(sp2)-Methyl Moiety         C8

Alert level G
REFLT03_ALERT_4_G Please check that the estimate of the number of Friedel pairs is
            correct. If it is not, please give the correct count in the
            _publ_section_exptl_refinement section of the submitted CIF.
           From the CIF: _diffrn_reflns_theta_max           25.01
           From the CIF: _reflns_number_total               1133
           Count of symmetry unique reflns         1134
           Completeness (_total/calc)             99.91%
           TEST3: Check Friedels for noncentro structure
           Estimate of Friedel pairs measured         0
           Fraction of Friedel pairs measured     0.000
           Are heavy atom types Z>Si present         no
PLAT199_ALERT_1_G Check the Reported _cell_measurement_temperature        293 K
PLAT200_ALERT_1_G Check the Reported _diffrn_ambient_temperature .        293 K

   0 ALERT level A = In general: serious problem
   0 ALERT level B = Potentially serious problem
   2 ALERT level C = Check and explain
   3 ALERT level G = General alerts; check

   3 ALERT type 1 CIF construction/syntax error, inconsistent or missing data
   0 ALERT type 2 Indicator that the structure model may be wrong or deficient
   0 ALERT type 3 Indicator that the structure quality may be low
   2 ALERT type 4 Improvement, methodology, query or suggestion
   0 ALERT type 5 Informative message, check

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Computing details

Data collection: SMART (Bruker, 2002); cell refinement: SAINT (Bruker, 2002); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 1997a); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997a); molecular graphics: SHELXTL (Sheldrick, 1997b) and PLATON (Spek, 2003); software used to prepare material for publication: SHELXL97.

(I)

Crystal data

C11H15NO3	F(000) = 448
Mr = 209.24	Dx = 1.315 Mg m^−3
Orthorhombic, P212121	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: P 2ac 2ab	Cell parameters from 2343 reflections
a = 6.2552 (5) Å	θ = 3.1–25.1°
b = 6.3403 (5) Å	µ = 0.10 mm^−1
c = 26.648 (2) Å	T = 293 K
V = 1056.86 (15) Å^3	Block, yellow
Z = 4	0.35 × 0.32 × 0.30 mm

Data collection

Bruker APEX area-dectector diffractometer	1133 independent reflections
Radiation source: fine-focus sealed tube	1061 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.019
φ and ω scans	θmax = 25.0°, θmin = 1.5°
Absorption correction: multi-scan (SADABS; Bruker, 2002)	h = −7→6
Tmin = 0.967, Tmax = 0.972	k = −7→6
5346 measured reflections	l = −31→27

Refinement

Refinement on F^2	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F^2 > 2σ(F^2)] = 0.037	Hydrogen site location: inferred from neighbouring sites
wR(F^2) = 0.126	H-atom parameters constrained
S = 1.02	w = 1/[σ^2(Fo^2) + (0.1088P)^2 + 0.0099P] where P = (Fo^2 + 2Fc^2)/3
1133 reflections	(Δ/σ)max = 0.001
136 parameters	Δρmax = 0.19 e Å^−3
0 restraints	Δρmin = −0.21 e Å^−3

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
C1	0.3704 (4)	0.9880 (4)	0.87938 (7)	0.0401 (5)
C2	0.2575 (4)	0.7950 (4)	0.87015 (7)	0.0384 (5)
C3	0.3345 (4)	0.6605 (4)	0.83177 (8)	0.0464 (6)
H3	0.2629	0.5346	0.8256	0.056*
C4	0.5088 (4)	0.7083 (4)	0.80358 (8)	0.0497 (6)
H4	0.5544	0.6173	0.7784	0.060*
C5	0.6193 (4)	0.8969 (4)	0.81298 (8)	0.0427 (6)
C6	0.5525 (4)	1.0333 (4)	0.84943 (8)	0.0436 (5)
H6	0.6275	1.1580	0.8547	0.052*
C7	0.0706 (4)	0.7411 (4)	0.89851 (8)	0.0383 (5)
C8	−0.0532 (4)	0.5432 (4)	0.88822 (9)	0.0513 (6)
H8A	−0.1724	0.5346	0.9108	0.077*
H8B	0.0380	0.4230	0.8930	0.077*
H8C	−0.1044	0.5452	0.8543	0.077*
C9	−0.1834 (4)	0.8454 (4)	0.96514 (9)	0.0475 (6)
H9A	−0.1690	0.7225	0.9866	0.057*
H9B	−0.3083	0.8259	0.9441	0.057*
C10	−0.2107 (4)	1.0399 (4)	0.99685 (8)	0.0475 (6)
H10A	−0.2038	1.1647	0.9759	0.057*
H10B	−0.3491	1.0372	1.0133	0.057*
C11	0.9172 (5)	1.1128 (5)	0.79080 (11)	0.0627 (8)
H11A	1.0346	1.1142	0.7676	0.094*
H11B	0.9712	1.1154	0.8245	0.094*
H11C	0.8288	1.2344	0.7852	0.094*
N1	0.0066 (3)	0.8679 (3)	0.93390 (7)	0.0416 (5)
H1	0.0850	0.9768	0.9395	0.050*
O1	0.3106 (3)	1.1180 (3)	0.91390 (7)	0.0569 (5)
O2	−0.0469 (3)	1.0458 (3)	1.03307 (7)	0.0596 (5)
H2A	−0.0689	1.1434	1.0526	0.089*
O3	0.7942 (3)	0.9268 (3)	0.78345 (6)	0.0558 (5)

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
C1	0.0436 (11)	0.0364 (12)	0.0403 (10)	0.0024 (10)	−0.0025 (9)	−0.0065 (9)
C2	0.0414 (11)	0.0376 (12)	0.0362 (10)	0.0017 (9)	−0.0048 (9)	−0.0036 (8)
C3	0.0529 (13)	0.0394 (12)	0.0469 (11)	−0.0028 (11)	−0.0069 (10)	−0.0113 (10)
C4	0.0539 (13)	0.0497 (14)	0.0454 (12)	0.0032 (12)	0.0026 (11)	−0.0160 (11)
C5	0.0437 (11)	0.0484 (13)	0.0361 (10)	0.0063 (11)	−0.0005 (9)	−0.0006 (10)
C6	0.0429 (11)	0.0390 (11)	0.0488 (11)	−0.0058 (10)	0.0004 (10)	−0.0053 (10)
C7	0.0407 (11)	0.0347 (11)	0.0394 (10)	0.0015 (9)	−0.0082 (9)	−0.0011 (9)
C8	0.0545 (14)	0.0438 (14)	0.0556 (13)	−0.0065 (13)	−0.0033 (11)	−0.0057 (11)
C9	0.0431 (12)	0.0491 (13)	0.0502 (12)	−0.0028 (11)	0.0049 (11)	−0.0022 (10)
C10	0.0435 (11)	0.0437 (12)	0.0552 (12)	0.0059 (12)	0.0110 (11)	0.0042 (11)
C11	0.0604 (15)	0.0636 (17)	0.0641 (15)	−0.0041 (14)	0.0149 (13)	0.0021 (13)
N1	0.0400 (10)	0.0401 (10)	0.0446 (10)	−0.0048 (9)	0.0013 (8)	−0.0045 (8)
O1	0.0583 (10)	0.0488 (10)	0.0635 (10)	−0.0132 (9)	0.0174 (9)	−0.0271 (8)
O2	0.0600 (10)	0.0545 (10)	0.0643 (10)	0.0098 (9)	−0.0022 (9)	−0.0192 (9)
O3	0.0556 (9)	0.0574 (11)	0.0546 (9)	−0.0034 (10)	0.0158 (8)	−0.0094 (8)

Geometric parameters (Å, º)

C1—O1	1.291 (3)	C8—H8B	0.96
C1—C6	1.420 (3)	C8—H8C	0.96
C1—C2	1.434 (3)	C9—N1	1.458 (3)
C2—C3	1.416 (3)	C9—C10	1.504 (3)
C2—C7	1.433 (3)	C9—H9A	0.97
C3—C4	1.359 (3)	C9—H9B	0.97
C3—H3	0.93	C10—O2	1.408 (3)
C4—C5	1.403 (4)	C10—H10A	0.97
C4—H4	0.93	C10—H10B	0.97
C5—O3	1.361 (3)	C11—O3	1.422 (4)
C5—C6	1.366 (3)	C11—H11A	0.96
C6—H6	0.93	C11—H11B	0.96
C7—N1	1.302 (3)	C11—H11C	0.96
C7—C8	1.500 (3)	N1—H1	0.86
C8—H8A	0.96	O2—H2A	0.82
O1—C1—C6	120.3 (2)	H8A—C8—H8C	109.5
O1—C1—C2	121.6 (2)	H8B—C8—H8C	109.5
C6—C1—C2	118.12 (19)	N1—C9—C10	109.47 (19)
C3—C2—C7	121.0 (2)	N1—C9—H9A	109.8
C3—C2—C1	118.0 (2)	C10—C9—H9A	109.8
C7—C2—C1	120.95 (19)	N1—C9—H9B	109.8
C4—C3—C2	122.5 (2)	C10—C9—H9B	109.8
C4—C3—H3	118.7	H9A—C9—H9B	108.2
C2—C3—H3	118.7	O2—C10—C9	108.9 (2)
C3—C4—C5	119.1 (2)	O2—C10—H10A	109.9
C3—C4—H4	120.4	C9—C10—H10A	109.9
C5—C4—H4	120.4	O2—C10—H10B	109.9
O3—C5—C6	124.7 (2)	C9—C10—H10B	109.9
O3—C5—C4	114.3 (2)	H10A—C10—H10B	108.3
C6—C5—C4	121.0 (2)	O3—C11—H11A	109.5
C5—C6—C1	121.1 (2)	O3—C11—H11B	109.5
C5—C6—H6	119.4	H11A—C11—H11B	109.5
C1—C6—H6	119.4	O3—C11—H11C	109.5
N1—C7—C2	119.1 (2)	H11A—C11—H11C	109.5
N1—C7—C8	119.3 (2)	H11B—C11—H11C	109.5
C2—C7—C8	121.6 (2)	C7—N1—C9	127.16 (19)
C7—C8—H8A	109.5	C7—N1—H1	116.4
C7—C8—H8B	109.5	C9—N1—H1	116.4
H8A—C8—H8B	109.5	C10—O2—H2A	109.5
C7—C8—H8C	109.5	C5—O3—C11	118.10 (19)
O1—C1—C2—C3	−179.6 (2)	C2—C1—C6—C5	−0.3 (3)
C6—C1—C2—C3	0.2 (3)	C3—C2—C7—N1	179.2 (2)
O1—C1—C2—C7	1.2 (3)	C1—C2—C7—N1	−1.6 (3)
C6—C1—C2—C7	−179.0 (2)	C3—C2—C7—C8	−1.1 (3)
C7—C2—C3—C4	178.8 (2)	C1—C2—C7—C8	178.1 (2)
C1—C2—C3—C4	−0.4 (3)	N1—C9—C10—O2	−69.5 (2)
C2—C3—C4—C5	0.7 (4)	C2—C7—N1—C9	177.14 (19)
C3—C4—C5—O3	178.5 (2)	C8—C7—N1—C9	−2.6 (3)
C3—C4—C5—C6	−0.8 (4)	C10—C9—N1—C7	−173.2 (2)
O3—C5—C6—C1	−178.6 (2)	C6—C5—O3—C11	0.0 (4)
C4—C5—C6—C1	0.7 (3)	C4—C5—O3—C11	−179.3 (2)
O1—C1—C6—C5	179.5 (2)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
O2—H2A···O1^i	0.82	1.91	2.708 (2)	164
N1—H1···O1	0.86	1.80	2.533 (3)	141

Symmetry code: (i) x−1/2, −y+5/2, −z+2.